NPASS Compound

Structure

CID106601 OpenBabel06191715452D 84 96 0 0 1 0 0 0 0 0999 V2000 6.6422 2.8744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8289 5.2726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8116 0.4780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7749 -1.2761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4721 2.3950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8286 6.2311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6416 -0.0015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3867 -2.0137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4726 4.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4891 5.2730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9811 -0.9596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4974 -2.3358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4903 0.4804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4900 -3.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3201 1.9184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8294 -3.3552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9827 5.7505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4922 5.2718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6424 3.8330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6591 4.7935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9814 -0.0011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8302 -1.4372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3203 0.9598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6596 -3.8348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1524 5.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3024 2.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6586 6.7106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6414 -0.9601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0538 -2.9123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3225 5.7509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3026 3.8325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4888 6.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8111 -1.4391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1092 -3.0734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6601 0.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4902 -2.3967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4920 4.3133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8127 5.2710 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4898 2.3974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8295 -2.3965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6599 1.9179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6599 -1.9172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3220 3.8338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8296 2.3970 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3215 1.9168 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6601 -0.9586 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4910 1.4376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8304 1.4380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6603 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6608 1.9172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8294 3.3555 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1517 1.4372 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8124 4.3125 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6594 3.8350 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1514 0.4784 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1522 4.3129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4908 0.4788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8301 0.4793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 -0.4793 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0002 -0.9583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1506 0.4808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6594 -4.7933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1324 2.3945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6584 7.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4714 -1.4395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6656 -3.6499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3227 6.7094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1329 4.3116 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3188 6.7110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8109 -2.3976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7763 -3.9720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8301 0.4799 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3203 -1.9176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6617 3.8343 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6429 5.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6611 2.8757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0009 3.8346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9819 1.9162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8300 0.4792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4896 3.3560 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9822 3.8334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3210 -0.0008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0004 -1.9169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 19 1 0 0 0 0 2 6 2 0 0 0 0 2 20 1 0 0 0 0 3 7 2 0 0 0 0 3 21 1 0 0 0 0 4 8 2 0 0 0 0 4 22 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 29 1 0 0 0 0 9 19 2 0 0 0 0 9 31 1 0 0 0 0 10 20 2 0 0 0 0 10 32 1 0 0 0 0 11 21 2 0 0 0 0 11 33 1 0 0 0 0 12 22 2 0 0 0 0 12 34 1 0 0 0 0 13 23 2 0 0 0 0 13 35 1 0 0 0 0 14 24 2 0 0 0 0 14 36 1 0 0 0 0 15 23 1 0 0 0 0 15 39 2 0 0 0 0 16 24 1 0 0 0 0 16 40 2 0 0 0 0 17 25 1 0 0 0 0 17 38 1 0 0 0 0 18 30 2 0 0 0 0 18 37 1 0 0 0 0 23 61 1 0 0 0 0 24 62 1 0 0 0 0 25 30 1 0 0 0 0 25 56 2 0 0 0 0 26 31 2 0 0 0 0 26 63 1 0 0 0 0 27 32 2 0 0 0 0 27 64 1 0 0 0 0 28 33 2 0 0 0 0 28 65 1 0 0 0 0 29 34 2 0 0 0 0 29 66 1 0 0 0 0 30 67 1 0 0 0 0 31 68 1 0 0 0 0 32 69 1 0 0 0 0 33 70 1 0 0 0 0 34 71 1 0 0 0 0 35 41 2 0 0 0 0 35 72 1 0 0 0 0 36 42 2 0 0 0 0 36 73 1 0 0 0 0 37 43 2 0 0 0 0 37 74 1 0 0 0 0 38 53 1 0 0 0 0 38 75 1 6 0 0 0 39 41 1 0 0 0 0 39 80 1 0 0 0 0 40 42 1 0 0 0 0 40 83 1 0 0 0 0 41 44 1 0 0 0 0 43 56 1 0 0 0 0 44 48 1 1 0 0 0 44 51 1 0 0 0 0 45 43 1 6 0 0 0 45 47 1 0 0 0 0 45 52 1 0 0 0 0 46 42 1 1 0 0 0 46 49 1 0 0 0 0 46 59 1 0 0 0 0 47 50 2 0 0 0 0 47 57 1 0 0 0 0 48 50 1 0 0 0 0 48 58 2 0 0 0 0 49 57 2 0 0 0 0 49 58 1 0 0 0 0 50 76 1 0 0 0 0 51 54 1 0 0 0 0 51 77 1 6 0 0 0 52 55 1 0 0 0 0 52 78 1 1 0 0 0 53 19 1 1 0 0 0 53 81 1 0 0 0 0 54 20 1 6 0 0 0 54 80 1 0 0 0 0 55 21 1 1 0 0 0 55 82 1 0 0 0 0 56 81 1 0 0 0 0 57 82 1 0 0 0 0 58 84 1 0 0 0 0 59 60 1 6 0 0 0 59 79 1 0 0 0 0 60 22 1 6 0 0 0 60 83 1 0 0 0 0 60 84 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1152.25
Volume:	1082.772
LogP:	5.271
LogD:	1.791
LogS:	-4.264
# Rotatable Bonds:	6
TPSA:	430.52
# H-Bond Aceptor:	24
# H-Bond Donor:	19
# Rings:	13
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	7.156
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.411
MDCK Permeability:	1.5619750683981692e-06
Pgp-inhibitor:	0.399
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	83.20774841308594%
Volume Distribution (VD):	-0.036
Pgp-substrate:	31.798389434814453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.029
CYP2C9-inhibitor:	0.117
CYP2C9-substrate:	0.987
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.633

ADMET: Excretion

Clearance (CL):	9.167
Half-life (T1/2):	0.326

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.872
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.978
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.94
Respiratory Toxicity:	0.002

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC106601

Natural Product ID:	NPC106601
*Common Name:**	Cassiatannin A
IUPAC Name:	n.a.
Synonyms:	Cassiatannin A
Standard InCHIKey:	MIKRORKCMXNOCX-IATHEQPCSA-N
Standard InCHI:	InChI=1S/C60H48O24/c61-23-13-35(72)41-39(15-23)80-54(20-2-6-27(64)32(69)10-20)51(77)44(41)48-50(76)47-45(43-37(74)18-30(67)25-17-38(75)53(81-56(25)43)19-1-5-26(63)31(68)9-19)52(78)55(21-3-7-28(65)33(70)11-21)82-57(47)49-46-42-36(73)14-24(62)16-40(42)83-60(59(46)79,84-58(48)49)22-4-8-29(66)34(71)12-22/h1-16,18,38,44-46,51-55,59,61-79H,17H2/t38-,44+,45-,46+,51+,52+,53+,54+,55+,59+,60-/m0/s1
SMILES:	Oc1cc(O)c2c(c1)O[C@@H]([C@@H]([C@H]2c1c(O)c2[C@@H]([C@@H](O)[C@H](Oc2c2c1O[C@@]1(Oc3c([C@H]2[C@H]1O)c(O)cc(c3)O)c1ccc(c(c1)O)O)c1ccc(c(c1)O)O)c1c(O)cc(c2c1O[C@@H]([C@H](C2)O)c1ccc(c(c1)O)O)O)O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823107
PubChem CID:	44610605
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21875098]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24868863]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25089845]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28682072]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[29883114]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	38.0	%	PMID[458401]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	52.0	%	PMID[458401]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	97.0	%	PMID[458401]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC106601 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	539
0.1-0.2	1880
0.2-0.3	5057
0.3-0.4	11404
0.4-0.5	6610
0.5-0.6	4868
0.6-0.7	7058
0.7-0.8	4401
0.8-0.85	696
0.85-0.9	122
0.9-0.95	34
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC212614
1.0	High Similarity	NPC471404
1.0	High Similarity	NPC151474
1.0	High Similarity	NPC205613
1.0	High Similarity	NPC86630
1.0	High Similarity	NPC159526
0.9933	High Similarity	NPC73517
0.9933	High Similarity	NPC147743
0.9933	High Similarity	NPC4809
0.9737	High Similarity	NPC185231
0.9733	High Similarity	NPC46335
0.9667	High Similarity	NPC224161
0.96	High Similarity	NPC279406
0.96	High Similarity	NPC226809
0.96	High Similarity	NPC272552
0.96	High Similarity	NPC134911
0.96	High Similarity	NPC46283
0.96	High Similarity	NPC322899
0.96	High Similarity	NPC44192
0.96	High Similarity	NPC469944
0.96	High Similarity	NPC226108
0.9533	High Similarity	NPC471403
0.9408	High Similarity	NPC20050
0.9408	High Similarity	NPC306267
0.9299	High Similarity	NPC12326
0.9276	High Similarity	NPC259707
0.9267	High Similarity	NPC18185
0.9267	High Similarity	NPC58190
0.9267	High Similarity	NPC262911
0.9267	High Similarity	NPC294558
0.9267	High Similarity	NPC82917
0.9267	High Similarity	NPC170103
0.9267	High Similarity	NPC204770
0.9267	High Similarity	NPC263940
0.9267	High Similarity	NPC108811
0.9267	High Similarity	NPC236202
0.9267	High Similarity	NPC202742
0.9267	High Similarity	NPC70409
0.9211	High Similarity	NPC477612
0.92	High Similarity	NPC102280
0.92	High Similarity	NPC155564
0.92	High Similarity	NPC96576
0.92	High Similarity	NPC248053
0.9172	High Similarity	NPC1253
0.9172	High Similarity	NPC100936
0.915	High Similarity	NPC473621
0.9145	High Similarity	NPC211561
0.9091	High Similarity	NPC59692
0.9079	High Similarity	NPC20757
0.9079	High Similarity	NPC280945
0.9079	High Similarity	NPC227516
0.894	High Similarity	NPC171932
0.894	High Similarity	NPC28440
0.8889	High Similarity	NPC473480
0.8889	High Similarity	NPC9309
0.8889	High Similarity	NPC15538
0.8867	High Similarity	NPC277331
0.8867	High Similarity	NPC178054
0.8867	High Similarity	NPC100482
0.8854	High Similarity	NPC157333
0.8846	High Similarity	NPC233467
0.8831	High Similarity	NPC281549
0.8816	High Similarity	NPC168579
0.8816	High Similarity	NPC469313
0.8816	High Similarity	NPC138227
0.8816	High Similarity	NPC76176
0.8816	High Similarity	NPC475492
0.8782	High Similarity	NPC329343
0.8782	High Similarity	NPC324517
0.8782	High Similarity	NPC321972
0.8774	High Similarity	NPC321657
0.8774	High Similarity	NPC318373
0.875	High Similarity	NPC37793
0.8718	High Similarity	NPC472710
0.8718	High Similarity	NPC472709
0.8706	High Similarity	NPC318119
0.8701	High Similarity	NPC125755
0.8701	High Similarity	NPC150714
0.8701	High Similarity	NPC260397
0.8701	High Similarity	NPC95652
0.8693	High Similarity	NPC225445
0.8679	High Similarity	NPC202104
0.8675	High Similarity	NPC262189
0.8654	High Similarity	NPC470826
0.8654	High Similarity	NPC473266
0.8654	High Similarity	NPC476969
0.8654	High Similarity	NPC470098
0.8647	High Similarity	NPC321916
0.8642	High Similarity	NPC48880
0.8636	High Similarity	NPC277867
0.8636	High Similarity	NPC161700
0.8636	High Similarity	NPC475096
0.8636	High Similarity	NPC181615
0.8634	High Similarity	NPC470828
0.8627	High Similarity	NPC116922
0.8608	High Similarity	NPC21902
0.8599	High Similarity	NPC225815
0.8599	High Similarity	NPC9933
0.8599	High Similarity	NPC260781
0.8599	High Similarity	NPC185955
0.8599	High Similarity	NPC469707
0.8599	High Similarity	NPC214326
0.8599	High Similarity	NPC145979
0.8599	High Similarity	NPC218041
0.8599	High Similarity	NPC469706
0.8599	High Similarity	NPC182368
0.859	High Similarity	NPC270751
0.8581	High Similarity	NPC190714
0.8581	High Similarity	NPC99515
0.8571	High Similarity	NPC473108
0.8571	High Similarity	NPC470827
0.8571	High Similarity	NPC15659
0.8571	High Similarity	NPC304894
0.8571	High Similarity	NPC125495
0.8553	High Similarity	NPC291101
0.8553	High Similarity	NPC22317
0.8553	High Similarity	NPC266197
0.8553	High Similarity	NPC78809
0.8545	High Similarity	NPC59516
0.8543	High Similarity	NPC470308
0.8543	High Similarity	NPC474390
0.8543	High Similarity	NPC470307
0.8535	High Similarity	NPC295573
0.8535	High Similarity	NPC470208
0.8526	High Similarity	NPC328567
0.8526	High Similarity	NPC327412
0.8526	High Similarity	NPC15956
0.8526	High Similarity	NPC262297
0.8526	High Similarity	NPC114505
0.8526	High Similarity	NPC193473
0.8526	High Similarity	NPC224674
0.8526	High Similarity	NPC320671
0.8526	High Similarity	NPC39657
0.8526	High Similarity	NPC174251
0.8526	High Similarity	NPC320970
0.8526	High Similarity	NPC275284
0.8526	High Similarity	NPC153182
0.8526	High Similarity	NPC213074
0.8526	High Similarity	NPC227902
0.8526	High Similarity	NPC31325
0.8519	High Similarity	NPC166456
0.8519	High Similarity	NPC98083
0.8519	High Similarity	NPC7543
0.8519	High Similarity	NPC24339
0.8519	High Similarity	NPC94220
0.8512	High Similarity	NPC98583
0.8506	High Similarity	NPC113680
0.8506	High Similarity	NPC278961
0.8506	High Similarity	NPC473044
0.8506	High Similarity	NPC163508
0.8506	High Similarity	NPC173203
0.85	High Similarity	NPC8712
0.8497	Intermediate Similarity	NPC89686
0.8497	Intermediate Similarity	NPC469661
0.8497	Intermediate Similarity	NPC273932
0.8497	Intermediate Similarity	NPC257095
0.8491	Intermediate Similarity	NPC476391
0.8491	Intermediate Similarity	NPC157783
0.8491	Intermediate Similarity	NPC325860
0.8487	Intermediate Similarity	NPC70682
0.8487	Intermediate Similarity	NPC260741
0.8477	Intermediate Similarity	NPC470802
0.8477	Intermediate Similarity	NPC471522
0.8471	Intermediate Similarity	NPC473876
0.8471	Intermediate Similarity	NPC175976
0.8471	Intermediate Similarity	NPC304048
0.8471	Intermediate Similarity	NPC329836
0.8471	Intermediate Similarity	NPC226153
0.8462	Intermediate Similarity	NPC317053
0.8462	Intermediate Similarity	NPC324492
0.8462	Intermediate Similarity	NPC14468
0.8462	Intermediate Similarity	NPC274454
0.8462	Intermediate Similarity	NPC215678
0.8452	Intermediate Similarity	NPC65333
0.8452	Intermediate Similarity	NPC100251
0.8452	Intermediate Similarity	NPC473045
0.8452	Intermediate Similarity	NPC177597
0.8452	Intermediate Similarity	NPC25292
0.8442	Intermediate Similarity	NPC5262
0.8442	Intermediate Similarity	NPC475084
0.8442	Intermediate Similarity	NPC472714
0.8442	Intermediate Similarity	NPC475891
0.8442	Intermediate Similarity	NPC469559
0.8442	Intermediate Similarity	NPC189115
0.8442	Intermediate Similarity	NPC59841
0.8442	Intermediate Similarity	NPC204347
0.8442	Intermediate Similarity	NPC2613
0.8438	Intermediate Similarity	NPC106669
0.8438	Intermediate Similarity	NPC475227
0.8438	Intermediate Similarity	NPC200645
0.8431	Intermediate Similarity	NPC61783
0.8431	Intermediate Similarity	NPC20520
0.8431	Intermediate Similarity	NPC106944
0.843	Intermediate Similarity	NPC132111
0.8428	Intermediate Similarity	NPC302915
0.8428	Intermediate Similarity	NPC2745
0.8421	Intermediate Similarity	NPC211549
0.8418	Intermediate Similarity	NPC55158
0.8418	Intermediate Similarity	NPC286235
0.8418	Intermediate Similarity	NPC95392

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC106601 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	432
0.1-0.2	930
0.2-0.3	2089
0.3-0.4	2758
0.4-0.5	1539
0.5-0.6	909
0.6-0.7	424
0.7-0.8	66
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD1613	Approved
0.8333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD8455	Phase 2
0.8079	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7074	Phase 3
0.7953	Intermediate Similarity	NPD7228	Approved
0.7947	Intermediate Similarity	NPD4908	Phase 1
0.7919	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6674	Discontinued
0.7895	Intermediate Similarity	NPD3027	Phase 3
0.7861	Intermediate Similarity	NPD7472	Approved
0.7803	Intermediate Similarity	NPD7054	Approved
0.7784	Intermediate Similarity	NPD8313	Approved
0.7784	Intermediate Similarity	NPD8312	Approved
0.7771	Intermediate Similarity	NPD7251	Discontinued
0.7744	Intermediate Similarity	NPD1653	Approved
0.7738	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6166	Phase 2
0.7727	Intermediate Similarity	NPD7808	Phase 3
0.7714	Intermediate Similarity	NPD6797	Phase 2
0.7647	Intermediate Similarity	NPD6234	Discontinued
0.76	Intermediate Similarity	NPD1610	Phase 2
0.76	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7240	Approved
0.7562	Intermediate Similarity	NPD7266	Discontinued
0.756	Intermediate Similarity	NPD37	Approved
0.7558	Intermediate Similarity	NPD7199	Phase 2
0.7529	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD4966	Approved
0.7529	Intermediate Similarity	NPD4965	Approved
0.7515	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD3818	Discontinued
0.7419	Intermediate Similarity	NPD2861	Phase 2
0.7401	Intermediate Similarity	NPD5844	Phase 1
0.7389	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1091	Approved
0.7356	Intermediate Similarity	NPD6959	Discontinued
0.7353	Intermediate Similarity	NPD1934	Approved
0.7348	Intermediate Similarity	NPD8053	Approved
0.7348	Intermediate Similarity	NPD8054	Approved
0.7333	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4625	Phase 3
0.7314	Intermediate Similarity	NPD3787	Discontinued
0.7278	Intermediate Similarity	NPD6559	Discontinued
0.7277	Intermediate Similarity	NPD7680	Approved
0.7267	Intermediate Similarity	NPD7097	Phase 1
0.7256	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4380	Phase 2
0.7225	Intermediate Similarity	NPD7768	Phase 2
0.7219	Intermediate Similarity	NPD1548	Phase 1
0.7213	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4060	Phase 1
0.7184	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4749	Approved
0.7158	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7447	Phase 1
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5058	Phase 3
0.7115	Intermediate Similarity	NPD8651	Approved
0.711	Intermediate Similarity	NPD1465	Phase 2
0.7102	Intermediate Similarity	NPD5494	Approved
0.7095	Intermediate Similarity	NPD7473	Discontinued
0.7092	Intermediate Similarity	NPD8151	Discontinued
0.7086	Intermediate Similarity	NPD7075	Discontinued
0.7083	Intermediate Similarity	NPD7212	Phase 2
0.7083	Intermediate Similarity	NPD7213	Phase 3
0.7056	Intermediate Similarity	NPD3751	Discontinued
0.7049	Intermediate Similarity	NPD7549	Discontinued
0.7041	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6232	Discontinued
0.7021	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8156	Discontinued
0.7011	Intermediate Similarity	NPD2801	Approved
0.7011	Intermediate Similarity	NPD7819	Suspended
0.6982	Remote Similarity	NPD1511	Approved
0.6981	Remote Similarity	NPD3018	Phase 2
0.6975	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3620	Phase 2
0.6966	Remote Similarity	NPD8127	Discontinued
0.6961	Remote Similarity	NPD8099	Discontinued
0.6961	Remote Similarity	NPD8252	Approved
0.6961	Remote Similarity	NPD8251	Approved
0.6951	Remote Similarity	NPD4536	Approved
0.6951	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4538	Approved
0.6935	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7783	Phase 2
0.6918	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5960	Phase 3
0.6909	Remote Similarity	NPD5588	Approved
0.6902	Remote Similarity	NPD7685	Pre-registration
0.6901	Remote Similarity	NPD1512	Approved
0.6897	Remote Similarity	NPD7411	Suspended
0.6897	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3817	Phase 2
0.6862	Remote Similarity	NPD7906	Approved
0.6852	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1652	Phase 2
0.6836	Remote Similarity	NPD3882	Suspended
0.6835	Remote Similarity	NPD2983	Phase 2
0.6835	Remote Similarity	NPD2982	Phase 2
0.6833	Remote Similarity	NPD7229	Phase 3
0.6829	Remote Similarity	NPD5735	Approved
0.6826	Remote Similarity	NPD5763	Approved
0.6826	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5762	Approved
0.6821	Remote Similarity	NPD7843	Approved
0.6815	Remote Similarity	NPD3705	Approved
0.6809	Remote Similarity	NPD4663	Approved
0.6805	Remote Similarity	NPD8166	Discontinued
0.6805	Remote Similarity	NPD7466	Approved
0.6805	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7157	Approved
0.6791	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7041	Phase 2
0.6782	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7458	Discontinued
0.678	Remote Similarity	NPD5402	Approved
0.6776	Remote Similarity	NPD5283	Phase 1
0.6774	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2981	Phase 2
0.6766	Remote Similarity	NPD6100	Approved
0.6766	Remote Similarity	NPD6099	Approved
0.6765	Remote Similarity	NPD6190	Approved
0.6763	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6801	Discontinued
0.6748	Remote Similarity	NPD6798	Discontinued
0.6747	Remote Similarity	NPD7119	Phase 2
0.6744	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7313	Approved
0.6738	Remote Similarity	NPD7310	Approved
0.6738	Remote Similarity	NPD4577	Approved
0.6738	Remote Similarity	NPD7311	Approved
0.6738	Remote Similarity	NPD4578	Approved
0.6738	Remote Similarity	NPD7312	Approved
0.673	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6355	Discontinued
0.6726	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD7871	Phase 2
0.6717	Remote Similarity	NPD7870	Phase 2
0.6707	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3750	Approved
0.6706	Remote Similarity	NPD3892	Phase 2
0.6702	Remote Similarity	NPD7309	Approved
0.6688	Remote Similarity	NPD5125	Phase 3
0.6688	Remote Similarity	NPD6516	Phase 2
0.6688	Remote Similarity	NPD5846	Approved
0.6688	Remote Similarity	NPD6671	Approved
0.6688	Remote Similarity	NPD5126	Approved
0.6687	Remote Similarity	NPD7095	Approved
0.6686	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1549	Phase 2
0.6685	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6843	Phase 3
0.6684	Remote Similarity	NPD6842	Approved
0.6684	Remote Similarity	NPD6841	Approved
0.6667	Remote Similarity	NPD27	Approved
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD2489	Approved
0.6648	Remote Similarity	NPD3051	Approved
0.6647	Remote Similarity	NPD5177	Phase 3
0.6645	Remote Similarity	NPD228	Approved
0.6624	Remote Similarity	NPD1357	Approved
0.6623	Remote Similarity	NPD3021	Approved
0.6623	Remote Similarity	NPD3022	Approved
0.6617	Remote Similarity	NPD7701	Phase 2
0.6616	Remote Similarity	NPD6823	Phase 2
0.6612	Remote Similarity	NPD2969	Approved
0.6612	Remote Similarity	NPD2970	Approved
0.6608	Remote Similarity	NPD6331	Phase 2
0.6607	Remote Similarity	NPD4108	Discontinued
0.6606	Remote Similarity	NPD6233	Phase 2
0.6605	Remote Similarity	NPD6584	Phase 3
0.6604	Remote Similarity	NPD422	Phase 1
0.6599	Remote Similarity	NPD6782	Approved
0.6599	Remote Similarity	NPD6780	Approved
0.6599	Remote Similarity	NPD6776	Approved
0.6599	Remote Similarity	NPD6779	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data