NPASS Compound

Structure

NPC471090 OpenBabel07101719182D 87 96 0 0 1 0 0 0 0 0999 V2000 2.2990 2.9723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8468 5.2663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4284 -7.9175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2193 -2.8365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2090 -2.8365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3117 1.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3117 -0.9041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2352 3.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9293 2.4425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2032 3.5896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8571 -1.4845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2372 0.4948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5713 -0.4948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6554 -0.3058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7142 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8571 1.4845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7142 -6.9278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5710 0.9897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1426 0.9897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7142 -2.9691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8571 0.4948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9613 2.2368 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5091 4.5308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2855 -7.4227 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6554 1.2955 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8571 -6.4330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5710 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1426 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5713 -3.4639 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8571 -1.4845 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8571 -0.4948 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5713 -1.4845 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1426 -7.9175 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -6.9278 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4281 -0.4948 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5713 -4.4536 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9997 -0.4948 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9997 -7.4227 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8571 -6.4330 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4281 -1.4845 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4284 -4.9485 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8571 -5.4433 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9997 -6.4330 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5710 -1.9794 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9997 -1.4845 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2855 -4.4536 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1426 -1.9794 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4771 4.7366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.9485 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1426 -5.9381 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7139 -1.4845 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2855 -3.4639 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2855 -1.4845 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7142 -1.9794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7142 0.9897 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7142 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8571 -0.4948 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7142 -7.9175 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7139 1.4845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2855 1.4845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1426 -8.9072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -7.9175 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2852 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7142 -4.9485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8568 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8568 -7.9175 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7142 -6.9278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2852 -1.9794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4284 -5.9381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7142 -4.9485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8568 -5.9381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5710 -2.9691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7830 5.6778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1394 4.0011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.9588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2855 -6.4330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8571 -5.4433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7139 -0.4948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2855 -0.4948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4284 -2.9691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4284 -1.9794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8568 -1.9794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1426 -4.9485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1426 -2.9691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 4 56 1 0 0 0 0 5 56 1 0 0 0 0 6 57 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 24 1 0 0 0 0 10 25 2 0 0 0 0 11 12 1 0 0 0 0 11 32 1 0 0 0 0 12 33 1 0 0 0 0 13 15 1 0 0 0 0 13 27 1 0 0 0 0 14 16 1 0 0 0 0 14 34 1 0 0 0 0 15 58 1 0 0 0 0 16 59 1 0 0 0 0 17 18 1 0 0 0 0 17 57 1 0 0 0 0 19 61 1 0 0 0 0 20 62 1 0 0 0 0 21 63 1 0 0 0 0 22 78 1 0 0 0 0 23 59 1 0 0 0 0 23 60 1 0 0 0 0 24 1 1 6 0 0 0 24 27 1 0 0 0 0 25 50 1 0 0 0 0 26 3 1 1 0 0 0 26 35 1 0 0 0 0 26 79 1 0 0 0 0 27 57 1 1 0 0 0 28 19 1 6 0 0 0 28 36 1 0 0 0 0 28 80 1 0 0 0 0 29 20 1 1 0 0 0 29 37 1 0 0 0 0 29 81 1 0 0 0 0 30 21 1 6 0 0 0 30 39 1 0 0 0 0 30 82 1 0 0 0 0 31 22 1 6 0 0 0 31 38 1 0 0 0 0 31 83 1 0 0 0 0 32 56 1 0 0 0 0 32 59 1 1 0 0 0 33 58 1 6 0 0 0 33 60 1 0 0 0 0 34 56 1 0 0 0 0 34 84 1 1 0 0 0 35 40 1 0 0 0 0 35 64 1 6 0 0 0 36 41 1 0 0 0 0 36 65 1 1 0 0 0 37 42 1 0 0 0 0 37 66 1 6 0 0 0 38 43 1 0 0 0 0 38 67 1 1 0 0 0 39 47 1 0 0 0 0 39 68 1 1 0 0 0 40 45 1 0 0 0 0 40 69 1 1 0 0 0 41 44 1 0 0 0 0 41 70 1 6 0 0 0 42 46 1 0 0 0 0 42 71 1 1 0 0 0 43 48 1 0 0 0 0 43 72 1 6 0 0 0 44 51 1 0 0 0 0 44 73 1 1 0 0 0 45 52 1 0 0 0 0 45 74 1 1 0 0 0 46 53 1 0 0 0 0 46 75 1 6 0 0 0 47 49 1 0 0 0 0 47 85 1 6 0 0 0 48 54 1 0 0 0 0 48 86 1 1 0 0 0 49 55 1 0 0 0 0 49 87 1 1 0 0 0 50 76 2 0 0 0 0 50 77 1 0 0 0 0 51 78 1 6 0 0 0 51 80 1 0 0 0 0 52 79 1 0 0 0 0 52 86 1 6 0 0 0 53 81 1 0 0 0 0 53 85 1 1 0 0 0 54 83 1 0 0 0 0 54 87 1 6 0 0 0 55 82 1 0 0 0 0 55 84 1 6 0 0 0 57 58 1 1 0 0 0 58 7 1 6 0 0 0 59 60 1 6 0 0 0 60 18 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1248.61
Volume:	1190.178
LogP:	-0.252
LogD:	0.619
LogS:	-2.848
# Rotatable Bonds:	18
TPSA:	433.05
# H-Bond Aceptor:	27
# H-Bond Donor:	16
# Rings:	10
# Heavy Atoms:	27

MedChem Properties

QED Drug-Likeness Score:	0.049
Synthetic Accessibility Score:	5.361
Fsp3:	0.917
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.641
MDCK Permeability:	0.00030952616361901164
Pgp-inhibitor:	0.415
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.203
Plasma Protein Binding (PPB):	70.16056060791016%
Volume Distribution (VD):	-0.129
Pgp-substrate:	8.503143310546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	-0.371
Half-life (T1/2):	0.826

ADMET: Toxicity

hERG Blockers:	0.119
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.149
Maximum Recommended Daily Dose:	0.235
Skin Sensitization:	0.942
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC471090

Natural Product ID:	NPC471090
*Common Name:**	PKFILTNFIVXAID-MEEYSNSNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PKFILTNFIVXAID-MEEYSNSNSA-N
Standard InCHI:	InChI=1S/C60H96O27/c1-24(9-8-10-25(2)50(76)77)27-13-15-58(7)33-12-11-32-56(4,5)34(14-16-59(32)23-60(33,59)18-17-57(27,58)6)84-55-49(47(39(68)30(21-63)82-55)85-53-46(75)42(71)37(66)29(20-62)81-53)87-54-48(86-52-45(74)40(69)35(64)26(3)79-52)43(72)38(67)31(83-54)22-78-51-44(73)41(70)36(65)28(19-61)80-51/h8-10,24,26-49,51-55,61-75H,11-23H2,1-7H3,(H,76,77)/b9-8+,25-10+/t24-,26+,27-,28+,29-,30+,31-,32+,33+,34+,35+,36+,37-,38-,39+,40-,41-,42+,43+,44+,45-,46-,47-,48-,49+,51+,52+,53+,54+,55-,57-,58+,59-,60+/m1/s1
SMILES:	CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4CCC56CC57CCC8(C(CCC8(C7CCC6C4(C)C)C)C(C)C=CC=C(C)C(=O)O)C)CO)O)OC9C(C(C(C(O9)CO)O)O)O)COC1C(C(C(C(O1)CO)O)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2368569
PubChem CID:	73355976
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin glycosides

*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
NPO15083	Mussaenda macrophylla	Species	Rubiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[10543897]
NPO15083	Mussaenda macrophylla	Species	Rubiaceae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	=	156.0	ug.mL-1	PMID[489411]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	>	1250.0	ug.mL-1	PMID[489411]

☑ 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 NPC471090 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	272
0.1-0.2	1533
0.2-0.3	4865
0.3-0.4	11388
0.4-0.5	10912
0.5-0.6	6944
0.6-0.7	4221
0.7-0.8	1947
0.8-0.85	509
0.85-0.9	104
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9145	High Similarity	NPC135369
0.8803	High Similarity	NPC146652
0.8739	High Similarity	NPC470517
0.8739	High Similarity	NPC470915
0.8739	High Similarity	NPC470911
0.8678	High Similarity	NPC74259
0.8678	High Similarity	NPC474423
0.8655	High Similarity	NPC470515
0.8621	High Similarity	NPC65167
0.8618	High Similarity	NPC297950
0.8618	High Similarity	NPC179261
0.8607	High Similarity	NPC308262
0.8607	High Similarity	NPC117445
0.8607	High Similarity	NPC208193
0.8596	High Similarity	NPC234160
0.8595	High Similarity	NPC475419
0.8595	High Similarity	NPC475590
0.8595	High Similarity	NPC474908
0.8595	High Similarity	NPC120390
0.8522	High Similarity	NPC38217
0.8522	High Similarity	NPC159005
0.8522	High Similarity	NPC6931
0.8522	High Similarity	NPC472988
0.8512	High Similarity	NPC72260
0.848	Intermediate Similarity	NPC45606
0.848	Intermediate Similarity	NPC112492
0.848	Intermediate Similarity	NPC472268
0.848	Intermediate Similarity	NPC472270
0.848	Intermediate Similarity	NPC23020
0.848	Intermediate Similarity	NPC472269
0.848	Intermediate Similarity	NPC220838
0.8475	Intermediate Similarity	NPC473159
0.8448	Intermediate Similarity	NPC43976
0.8448	Intermediate Similarity	NPC51925
0.8448	Intermediate Similarity	NPC154085
0.8448	Intermediate Similarity	NPC296761
0.8448	Intermediate Similarity	NPC125361
0.8443	Intermediate Similarity	NPC40749
0.8443	Intermediate Similarity	NPC173555
0.8443	Intermediate Similarity	NPC314535
0.8435	Intermediate Similarity	NPC63368
0.8435	Intermediate Similarity	NPC231340
0.8435	Intermediate Similarity	NPC14946
0.8435	Intermediate Similarity	NPC208650
0.843	Intermediate Similarity	NPC292467
0.843	Intermediate Similarity	NPC55532
0.843	Intermediate Similarity	NPC470914
0.843	Intermediate Similarity	NPC470897
0.843	Intermediate Similarity	NPC32177
0.843	Intermediate Similarity	NPC30483
0.843	Intermediate Similarity	NPC469756
0.843	Intermediate Similarity	NPC236973
0.8425	Intermediate Similarity	NPC324933
0.8425	Intermediate Similarity	NPC475177
0.8425	Intermediate Similarity	NPC473679
0.8425	Intermediate Similarity	NPC233223
0.8425	Intermediate Similarity	NPC475444
0.8425	Intermediate Similarity	NPC196874
0.8425	Intermediate Similarity	NPC322904
0.8425	Intermediate Similarity	NPC183816
0.8425	Intermediate Similarity	NPC319719
0.8403	Intermediate Similarity	NPC469821
0.839	Intermediate Similarity	NPC472716
0.8374	Intermediate Similarity	NPC264336
0.8374	Intermediate Similarity	NPC193893
0.8362	Intermediate Similarity	NPC472896
0.8362	Intermediate Similarity	NPC180183
0.8362	Intermediate Similarity	NPC472897
0.8362	Intermediate Similarity	NPC246124
0.8361	Intermediate Similarity	NPC475556
0.8361	Intermediate Similarity	NPC475629
0.8361	Intermediate Similarity	NPC476670
0.8361	Intermediate Similarity	NPC470312
0.8348	Intermediate Similarity	NPC208594
0.8348	Intermediate Similarity	NPC269627
0.8348	Intermediate Similarity	NPC160816
0.8348	Intermediate Similarity	NPC69737
0.8348	Intermediate Similarity	NPC127801
0.8348	Intermediate Similarity	NPC165405
0.8348	Intermediate Similarity	NPC152584
0.8348	Intermediate Similarity	NPC473199
0.8348	Intermediate Similarity	NPC194842
0.8348	Intermediate Similarity	NPC208477
0.8347	Intermediate Similarity	NPC239293
0.8347	Intermediate Similarity	NPC472080
0.8346	Intermediate Similarity	NPC43589
0.8346	Intermediate Similarity	NPC222951
0.8346	Intermediate Similarity	NPC300655
0.8346	Intermediate Similarity	NPC311178
0.8333	Intermediate Similarity	NPC207637
0.8319	Intermediate Similarity	NPC307642
0.8305	Intermediate Similarity	NPC114188
0.8305	Intermediate Similarity	NPC472715
0.8293	Intermediate Similarity	NPC476675
0.8293	Intermediate Similarity	NPC475219
0.8293	Intermediate Similarity	NPC231518
0.8291	Intermediate Similarity	NPC302057
0.8279	Intermediate Similarity	NPC329905
0.8276	Intermediate Similarity	NPC181467
0.8264	Intermediate Similarity	NPC93883
0.8264	Intermediate Similarity	NPC20979
0.8264	Intermediate Similarity	NPC477807
0.8264	Intermediate Similarity	NPC471547
0.825	Intermediate Similarity	NPC100639
0.825	Intermediate Similarity	NPC294453
0.825	Intermediate Similarity	NPC261506
0.825	Intermediate Similarity	NPC70809
0.825	Intermediate Similarity	NPC473714
0.825	Intermediate Similarity	NPC476068
0.825	Intermediate Similarity	NPC79643
0.825	Intermediate Similarity	NPC60557
0.825	Intermediate Similarity	NPC204414
0.825	Intermediate Similarity	NPC471385
0.825	Intermediate Similarity	NPC475160
0.825	Intermediate Similarity	NPC119592
0.825	Intermediate Similarity	NPC250247
0.825	Intermediate Similarity	NPC4328
0.825	Intermediate Similarity	NPC471550
0.825	Intermediate Similarity	NPC65105
0.825	Intermediate Similarity	NPC71065
0.825	Intermediate Similarity	NPC54636
0.825	Intermediate Similarity	NPC293330
0.825	Intermediate Similarity	NPC298034
0.825	Intermediate Similarity	NPC123199
0.825	Intermediate Similarity	NPC224381
0.825	Intermediate Similarity	NPC76972
0.825	Intermediate Similarity	NPC477808
0.825	Intermediate Similarity	NPC43550
0.825	Intermediate Similarity	NPC305981
0.825	Intermediate Similarity	NPC227551
0.825	Intermediate Similarity	NPC475140
0.825	Intermediate Similarity	NPC57484
0.825	Intermediate Similarity	NPC41061
0.825	Intermediate Similarity	NPC309907
0.825	Intermediate Similarity	NPC161717
0.825	Intermediate Similarity	NPC236638
0.825	Intermediate Similarity	NPC202828
0.825	Intermediate Similarity	NPC469782
0.825	Intermediate Similarity	NPC67857
0.8246	Intermediate Similarity	NPC288694
0.8246	Intermediate Similarity	NPC312553
0.8246	Intermediate Similarity	NPC159036
0.822	Intermediate Similarity	NPC472717
0.8217	Intermediate Similarity	NPC316915
0.8211	Intermediate Similarity	NPC476150
0.8211	Intermediate Similarity	NPC308459
0.8211	Intermediate Similarity	NPC198325
0.8211	Intermediate Similarity	NPC170814
0.8211	Intermediate Similarity	NPC475358
0.8211	Intermediate Similarity	NPC207243
0.8211	Intermediate Similarity	NPC476127
0.8211	Intermediate Similarity	NPC474466
0.8211	Intermediate Similarity	NPC473566
0.8211	Intermediate Similarity	NPC475136
0.8211	Intermediate Similarity	NPC50689
0.8211	Intermediate Similarity	NPC233391
0.8211	Intermediate Similarity	NPC129393
0.8211	Intermediate Similarity	NPC268184
0.8205	Intermediate Similarity	NPC126147
0.8205	Intermediate Similarity	NPC220427
0.8205	Intermediate Similarity	NPC7213
0.8197	Intermediate Similarity	NPC473617
0.8197	Intermediate Similarity	NPC473828
0.819	Intermediate Similarity	NPC472900
0.819	Intermediate Similarity	NPC472898
0.819	Intermediate Similarity	NPC472899
0.819	Intermediate Similarity	NPC138057
0.8182	Intermediate Similarity	NPC63609
0.8182	Intermediate Similarity	NPC199428
0.8182	Intermediate Similarity	NPC5311
0.8182	Intermediate Similarity	NPC469820
0.8182	Intermediate Similarity	NPC469823
0.8182	Intermediate Similarity	NPC310341
0.8182	Intermediate Similarity	NPC193382
0.8182	Intermediate Similarity	NPC99620
0.8174	Intermediate Similarity	NPC155010
0.8174	Intermediate Similarity	NPC211879
0.8174	Intermediate Similarity	NPC120123
0.8174	Intermediate Similarity	NPC114874
0.8174	Intermediate Similarity	NPC472252
0.8174	Intermediate Similarity	NPC16573
0.8174	Intermediate Similarity	NPC8039
0.8174	Intermediate Similarity	NPC473198
0.8174	Intermediate Similarity	NPC189852
0.8174	Intermediate Similarity	NPC286969
0.8174	Intermediate Similarity	NPC31907
0.8174	Intermediate Similarity	NPC473020
0.8174	Intermediate Similarity	NPC16520
0.8174	Intermediate Similarity	NPC131479
0.8174	Intermediate Similarity	NPC157659
0.8174	Intermediate Similarity	NPC245280
0.8168	Intermediate Similarity	NPC127656
0.8167	Intermediate Similarity	NPC475467
0.8167	Intermediate Similarity	NPC192600
0.8167	Intermediate Similarity	NPC473826
0.8167	Intermediate Similarity	NPC114304
0.8167	Intermediate Similarity	NPC241909
0.8167	Intermediate Similarity	NPC295823
0.8167	Intermediate Similarity	NPC155410
0.8167	Intermediate Similarity	NPC166422

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 NPC471090 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	1575
0.2-0.3	4092
0.3-0.4	2238
0.4-0.5	598
0.5-0.6	287
0.6-0.7	100
0.7-0.8	19
0.8-0.85	4
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8512	High Similarity	NPD8294	Approved
0.8512	High Similarity	NPD8377	Approved
0.8443	Intermediate Similarity	NPD8379	Approved
0.8443	Intermediate Similarity	NPD8296	Approved
0.8443	Intermediate Similarity	NPD8378	Approved
0.8443	Intermediate Similarity	NPD8335	Approved
0.8443	Intermediate Similarity	NPD8380	Approved
0.8293	Intermediate Similarity	NPD8033	Approved
0.8293	Intermediate Similarity	NPD7503	Approved
0.8049	Intermediate Similarity	NPD7327	Approved
0.8049	Intermediate Similarity	NPD7328	Approved
0.7984	Intermediate Similarity	NPD7516	Approved
0.7869	Intermediate Similarity	NPD8133	Approved
0.7752	Intermediate Similarity	NPD7507	Approved
0.7603	Intermediate Similarity	NPD6686	Approved
0.7597	Intermediate Similarity	NPD8328	Phase 3
0.7576	Intermediate Similarity	NPD7319	Approved
0.7442	Intermediate Similarity	NPD8516	Approved
0.7442	Intermediate Similarity	NPD8515	Approved
0.7442	Intermediate Similarity	NPD8517	Approved
0.7377	Intermediate Similarity	NPD6412	Phase 2
0.7368	Intermediate Similarity	NPD7736	Approved
0.7311	Intermediate Similarity	NPD7640	Approved
0.7311	Intermediate Similarity	NPD7639	Approved
0.7308	Intermediate Similarity	NPD8513	Phase 3
0.7258	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD7638	Approved
0.7132	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD7115	Discovery
0.7008	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6370	Approved
0.6953	Remote Similarity	NPD8297	Approved
0.6953	Remote Similarity	NPD6882	Approved
0.6949	Remote Similarity	NPD8171	Discontinued
0.6942	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD8293	Discontinued
0.6889	Remote Similarity	NPD7492	Approved
0.687	Remote Similarity	NPD6009	Approved
0.6842	Remote Similarity	NPD6054	Approved
0.6842	Remote Similarity	NPD6319	Approved
0.6838	Remote Similarity	NPD6616	Approved
0.6803	Remote Similarity	NPD4225	Approved
0.68	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7078	Approved
0.678	Remote Similarity	NPD7838	Discovery
0.6774	Remote Similarity	NPD7632	Discontinued
0.6769	Remote Similarity	NPD4632	Approved
0.6757	Remote Similarity	NPD7625	Phase 1
0.6723	Remote Similarity	NPD7637	Suspended
0.6694	Remote Similarity	NPD5344	Discontinued
0.6691	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6641	Remote Similarity	NPD6881	Approved
0.6641	Remote Similarity	NPD6899	Approved
0.662	Remote Similarity	NPD8450	Suspended
0.6618	Remote Similarity	NPD5988	Approved
0.6615	Remote Similarity	NPD6649	Approved
0.6615	Remote Similarity	NPD6650	Approved
0.6615	Remote Similarity	NPD8130	Phase 1
0.6613	Remote Similarity	NPD6648	Approved
0.6612	Remote Similarity	NPD7748	Approved
0.6593	Remote Similarity	NPD6059	Approved
0.6589	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7902	Approved
0.6562	Remote Similarity	NPD5697	Approved
0.6549	Remote Similarity	NPD8449	Approved
0.6538	Remote Similarity	NPD7102	Approved
0.6538	Remote Similarity	NPD6883	Approved
0.6538	Remote Similarity	NPD7290	Approved
0.6525	Remote Similarity	NPD7524	Approved
0.6489	Remote Similarity	NPD6617	Approved
0.6489	Remote Similarity	NPD6847	Approved
0.6489	Remote Similarity	NPD6869	Approved
0.6484	Remote Similarity	NPD6402	Approved
0.6484	Remote Similarity	NPD7128	Approved
0.6484	Remote Similarity	NPD5739	Approved
0.6484	Remote Similarity	NPD6675	Approved
0.6462	Remote Similarity	NPD6013	Approved
0.6462	Remote Similarity	NPD6012	Approved
0.6462	Remote Similarity	NPD6372	Approved
0.6462	Remote Similarity	NPD6373	Approved
0.6462	Remote Similarity	NPD6014	Approved
0.6449	Remote Similarity	NPD6067	Discontinued
0.6446	Remote Similarity	NPD8034	Phase 2
0.6446	Remote Similarity	NPD7515	Phase 2
0.6446	Remote Similarity	NPD8035	Phase 2
0.6429	Remote Similarity	NPD8074	Phase 3
0.6423	Remote Similarity	NPD5983	Phase 2
0.6412	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7320	Approved
0.6385	Remote Similarity	NPD6011	Approved
0.6378	Remote Similarity	NPD5211	Phase 2
0.6357	Remote Similarity	NPD6336	Discontinued
0.6348	Remote Similarity	NPD7525	Registered
0.6341	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7900	Approved
0.6325	Remote Similarity	NPD6695	Phase 3
0.6311	Remote Similarity	NPD6079	Approved
0.6308	Remote Similarity	NPD5701	Approved
0.6293	Remote Similarity	NPD6902	Approved
0.6288	Remote Similarity	NPD4634	Approved
0.6279	Remote Similarity	NPD5141	Approved
0.626	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD7750	Discontinued
0.6231	Remote Similarity	NPD6008	Approved
0.623	Remote Similarity	NPD6698	Approved
0.623	Remote Similarity	NPD46	Approved
0.622	Remote Similarity	NPD5286	Approved
0.622	Remote Similarity	NPD4696	Approved
0.622	Remote Similarity	NPD5285	Approved
0.6218	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7830	Approved
0.6214	Remote Similarity	NPD7829	Approved
0.619	Remote Similarity	NPD6084	Phase 2
0.619	Remote Similarity	NPD6083	Phase 2
0.6183	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD7983	Approved
0.6165	Remote Similarity	NPD6371	Approved
0.6159	Remote Similarity	NPD7101	Approved
0.6159	Remote Similarity	NPD7100	Approved
0.6154	Remote Similarity	NPD6033	Approved
0.6148	Remote Similarity	NPD5328	Approved
0.6138	Remote Similarity	NPD7260	Phase 2
0.6136	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD7799	Discontinued
0.6124	Remote Similarity	NPD5224	Approved
0.6124	Remote Similarity	NPD4633	Approved
0.6124	Remote Similarity	NPD5226	Approved
0.6124	Remote Similarity	NPD5225	Approved
0.6121	Remote Similarity	NPD7645	Phase 2
0.6121	Remote Similarity	NPD6929	Approved
0.6119	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5222	Approved
0.6111	Remote Similarity	NPD5221	Approved
0.6087	Remote Similarity	NPD6335	Approved
0.6077	Remote Similarity	NPD5174	Approved
0.6077	Remote Similarity	NPD5175	Approved
0.6068	Remote Similarity	NPD6930	Phase 2
0.6068	Remote Similarity	NPD6931	Approved
0.6068	Remote Similarity	NPD7514	Phase 3
0.6066	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD4755	Approved
0.6063	Remote Similarity	NPD5173	Approved
0.6058	Remote Similarity	NPD6274	Approved
0.6058	Remote Similarity	NPD6868	Approved
0.6047	Remote Similarity	NPD5223	Approved
0.6042	Remote Similarity	NPD8336	Approved
0.6042	Remote Similarity	NPD8337	Approved
0.6034	Remote Similarity	NPD7145	Approved
0.6033	Remote Similarity	NPD3618	Phase 1
0.6032	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD4729	Approved
0.6015	Remote Similarity	NPD4730	Approved
0.6014	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD5778	Approved
0.5986	Remote Similarity	NPD8338	Approved
0.5971	Remote Similarity	NPD6314	Approved
0.5971	Remote Similarity	NPD6313	Approved
0.5969	Remote Similarity	NPD4700	Approved
0.5959	Remote Similarity	NPD5956	Approved
0.5956	Remote Similarity	NPD6053	Discontinued
0.5948	Remote Similarity	NPD6925	Approved
0.5948	Remote Similarity	NPD5776	Phase 2
0.5944	Remote Similarity	NPD8340	Approved
0.5944	Remote Similarity	NPD8299	Approved
0.5944	Remote Similarity	NPD8342	Approved
0.5944	Remote Similarity	NPD8341	Approved
0.5942	Remote Similarity	NPD6940	Discontinued
0.5935	Remote Similarity	NPD6672	Approved
0.5935	Remote Similarity	NPD5737	Approved
0.5932	Remote Similarity	NPD7332	Phase 2
0.5932	Remote Similarity	NPD6928	Phase 2
0.5926	Remote Similarity	NPD5248	Approved
0.5926	Remote Similarity	NPD5247	Approved
0.5926	Remote Similarity	NPD5249	Phase 3
0.5926	Remote Similarity	NPD5250	Approved
0.5926	Remote Similarity	NPD5251	Approved
0.592	Remote Similarity	NPD5281	Approved
0.592	Remote Similarity	NPD7087	Discontinued
0.592	Remote Similarity	NPD6411	Approved
0.592	Remote Similarity	NPD5284	Approved
0.5909	Remote Similarity	NPD7266	Discontinued
0.5906	Remote Similarity	NPD5695	Phase 3
0.5902	Remote Similarity	NPD5330	Approved
0.5902	Remote Similarity	NPD7521	Approved
0.5902	Remote Similarity	NPD6684	Approved
0.5902	Remote Similarity	NPD6409	Approved
0.5902	Remote Similarity	NPD7146	Approved
0.5902	Remote Similarity	NPD7334	Approved
0.5891	Remote Similarity	NPD5696	Approved
0.5887	Remote Similarity	NPD6051	Approved
0.5868	Remote Similarity	NPD4786	Approved
0.5865	Remote Similarity	NPD4767	Approved
0.5865	Remote Similarity	NPD4768	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