NPASS Compound

Structure

CID218801 OpenBabel06191716012D 68 79 0 0 1 0 0 0 0 0999 V2000 -4.9375 -4.0266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3022 -4.4517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9013 -0.5494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0671 -1.9943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8376 2.7375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2162 1.7977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7703 -0.9703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9362 -2.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1829 -4.9708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5476 -5.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7355 -1.0311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9013 -2.4759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3802 3.5334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7587 2.5936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6045 -1.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7703 -2.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5138 2.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1941 1.6771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2738 -2.9538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9057 -2.6070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9700 3.3303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3901 -4.1937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1977 -1.4144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4422 1.0478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9972 -3.7671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0671 -1.0311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2556 1.8697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9362 -1.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1486 1.8064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9896 -2.3093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4879 -5.6554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7355 -1.9943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3407 3.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6045 -2.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9245 3.4597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6048 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4740 -3.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1059 -3.5491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3187 -1.8377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4178 1.0478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2705 -0.4415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9543 0.2028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7065 -1.8377 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6447 -0.7871 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7379 1.0445 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7893 -1.3671 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5126 -1.2882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9056 0.2028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4644 0.1080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4422 -0.6421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7743 -1.5502 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8704 0.3484 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5854 -0.3153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4178 -0.6421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7131 1.0738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1020 -0.9703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7333 -6.5996 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5697 -2.4759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8833 4.2574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4387 -2.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2898 4.3510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6503 2.3096 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2418 -4.5405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0220 -3.8468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2468 -2.7983 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8994 1.8820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0422 0.1554 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 9 1 0 0 0 0 1 25 2 0 0 0 0 2 10 2 0 0 0 0 2 25 1 0 0 0 0 3 11 1 0 0 0 0 3 26 2 0 0 0 0 4 12 2 0 0 0 0 4 26 1 0 0 0 0 5 13 1 0 0 0 0 5 27 2 0 0 0 0 6 14 2 0 0 0 0 6 27 1 0 0 0 0 7 15 1 0 0 0 0 7 28 2 0 0 0 0 8 16 2 0 0 0 0 8 28 1 0 0 0 0 9 31 2 0 0 0 0 10 31 1 0 0 0 0 11 32 2 0 0 0 0 12 32 1 0 0 0 0 13 33 2 0 0 0 0 14 33 1 0 0 0 0 15 34 2 0 0 0 0 16 34 1 0 0 0 0 17 29 2 0 0 0 0 17 35 1 0 0 0 0 18 29 1 0 0 0 0 18 36 2 0 0 0 0 19 30 2 0 0 0 0 19 37 1 0 0 0 0 20 30 1 0 0 0 0 20 38 2 0 0 0 0 21 35 2 0 0 0 0 21 36 1 0 0 0 0 22 37 2 0 0 0 0 22 38 1 0 0 0 0 23 39 2 0 0 0 0 23 41 1 0 0 0 0 24 40 2 0 0 0 0 24 42 1 0 0 0 0 31 57 1 0 0 0 0 32 58 1 0 0 0 0 33 59 1 0 0 0 0 34 60 1 0 0 0 0 35 61 1 0 0 0 0 36 62 1 0 0 0 0 37 63 1 0 0 0 0 38 64 1 0 0 0 0 39 47 1 0 0 0 0 39 65 1 0 0 0 0 40 48 1 0 0 0 0 40 66 1 0 0 0 0 41 49 2 0 0 0 0 41 67 1 0 0 0 0 42 50 2 0 0 0 0 42 68 1 0 0 0 0 43 25 1 6 0 0 0 43 47 1 0 0 0 0 43 51 1 0 0 0 0 44 26 1 1 0 0 0 44 51 1 0 0 0 0 44 52 1 0 0 0 0 45 29 1 6 0 0 0 45 49 1 0 0 0 0 45 55 1 0 0 0 0 46 30 1 6 0 0 0 46 50 1 0 0 0 0 46 56 1 0 0 0 0 47 53 2 0 0 0 0 48 54 2 0 0 0 0 49 53 1 0 0 0 0 50 54 1 0 0 0 0 51 54 1 6 0 0 0 52 48 1 6 0 0 0 52 53 1 0 0 0 0 55 27 1 1 0 0 0 55 67 1 0 0 0 0 56 28 1 1 0 0 0 56 68 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	906.27
Volume:	916.662
LogP:	8.133
LogD:	4.393
LogS:	-4.367
# Rotatable Bonds:	6
TPSA:	220.76
# H-Bond Aceptor:	12
# H-Bond Donor:	10
# Rings:	12
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.075
Synthetic Accessibility Score:	5.852
Fsp3:	0.143
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:	-6.613
MDCK Permeability:	3.4145298286603065e-06
Pgp-inhibitor:	0.711
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	97.82495880126953%
Volume Distribution (VD):	0.359
Pgp-substrate:	6.583981037139893%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.618
CYP2C19-inhibitor:	0.948
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.665
CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.487
CYP3A4-inhibitor:	0.165
CYP3A4-substrate:	0.583

ADMET: Excretion

Clearance (CL):	4.366
Half-life (T1/2):	0.348

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.425
Drug-inuced Liver Injury (DILI):	0.64
AMES Toxicity:	0.276
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.855
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.898
Respiratory Toxicity:	0.014

Download Data

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

Natural Product: NPC218801

Natural Product ID:	NPC218801
*Common Name:**	Vaticanol C
IUPAC Name:	n.a.
Synonyms:	Vaticanol C
Standard InCHIKey:	DTAYOOZOCCYGJM-UTFSVEQESA-N
Standard InCHI:	InChI=1S/C56H42O12/c57-31-9-1-25(2-10-31)43-47-39(65)23-41-49(45(29-17-35(61)21-36(62)18-29)55(67-41)27-5-13-33(59)14-6-27)53(47)52-44(26-3-11-32(58)12-4-26)51(43)54-48(52)40(66)24-42-50(54)46(30-19-37(63)22-38(64)20-30)56(68-42)28-7-15-34(60)16-8-28/h1-24,43-46,51-52,55-66H/t43-,44-,45-,46-,51-,52+,55+,56+/m1/s1
SMILES:	Oc1ccc(cc1)[C@@H]1[C@H]2[C@H](c3ccc(cc3)O)c3c([C@@H]1c1c2c2c(cc1O)O[C@H]([C@@H]2c1cc(O)cc(c1)O)c1ccc(cc1)O)c1c(cc3O)O[C@H]([C@@H]1c1cc(O)cc(c1)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224887
PubChem CID:	49866362
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO7794	Vatica albiramis	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20735051]
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	Eukaryota	Barks	n.a.	n.a.	PMID[22209731]
NPO25661	Vatica rassak	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25661	Vatica rassak	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25661	Vatica rassak	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7794	Vatica albiramis	Species	Dipterocarpaceae	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
IC50	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	IC50	=	94200.0	nM	PMID[566130]
NPT671	Individual Protein	Acidic alpha-glucosidase	Rattus norvegicus	IC50	=	140000.0	nM	PMID[566130]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	21200.0	nM	PMID[566130]

☑ 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 NPC218801 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	525
0.1-0.2	1720
0.2-0.3	4173
0.3-0.4	11478
0.4-0.5	7273
0.5-0.6	4744
0.6-0.7	8794
0.7-0.8	3446
0.8-0.85	372
0.85-0.9	125
0.9-0.95	30
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9792	High Similarity	NPC157081
0.9792	High Similarity	NPC233886
0.9792	High Similarity	NPC224528
0.9792	High Similarity	NPC105073
0.9724	High Similarity	NPC473018
0.9724	High Similarity	NPC120633
0.9653	High Similarity	NPC122980
0.9653	High Similarity	NPC177172
0.9653	High Similarity	NPC148516
0.9653	High Similarity	NPC180605
0.9653	High Similarity	NPC107862
0.965	High Similarity	NPC133209
0.965	High Similarity	NPC6702
0.965	High Similarity	NPC112819
0.9514	High Similarity	NPC111134
0.951	High Similarity	NPC149633
0.9444	High Similarity	NPC14468
0.931	High Similarity	NPC176804
0.931	High Similarity	NPC71686
0.9247	High Similarity	NPC231712
0.9247	High Similarity	NPC224921
0.9247	High Similarity	NPC237546
0.9247	High Similarity	NPC242774
0.9139	High Similarity	NPC202104
0.9073	High Similarity	NPC157333
0.9014	High Similarity	NPC11727
0.9014	High Similarity	NPC125579
0.9014	High Similarity	NPC15109
0.894	High Similarity	NPC476391
0.8889	High Similarity	NPC470308
0.8889	High Similarity	NPC470307
0.8819	High Similarity	NPC141717
0.8819	High Similarity	NPC471522
0.8767	High Similarity	NPC213607
0.8767	High Similarity	NPC273623
0.8767	High Similarity	NPC182509
0.8767	High Similarity	NPC174787
0.8658	High Similarity	NPC304894
0.8658	High Similarity	NPC15659
0.863	High Similarity	NPC71465
0.863	High Similarity	NPC472646
0.8621	High Similarity	NPC37410
0.8621	High Similarity	NPC258780
0.8601	High Similarity	NPC238168
0.8601	High Similarity	NPC473309
0.8601	High Similarity	NPC237424
0.8591	High Similarity	NPC163508
0.8591	High Similarity	NPC173203
0.8571	High Similarity	NPC233467
0.8571	High Similarity	NPC59692
0.8562	High Similarity	NPC472648
0.8562	High Similarity	NPC472649
0.8562	High Similarity	NPC206525
0.8562	High Similarity	NPC133463
0.8562	High Similarity	NPC191462
0.8562	High Similarity	NPC472647
0.8562	High Similarity	NPC170328
0.8553	High Similarity	NPC227516
0.8553	High Similarity	NPC20757
0.8552	High Similarity	NPC476617
0.8552	High Similarity	NPC476615
0.8552	High Similarity	NPC473107
0.8552	High Similarity	NPC476616
0.8531	High Similarity	NPC254000
0.8506	High Similarity	NPC329343
0.8506	High Similarity	NPC321972
0.8506	High Similarity	NPC324517
0.8491	Intermediate Similarity	NPC48880
0.8491	Intermediate Similarity	NPC90822
0.8487	Intermediate Similarity	NPC153182
0.8487	Intermediate Similarity	NPC174251
0.8483	Intermediate Similarity	NPC469610
0.8472	Intermediate Similarity	NPC8899
0.8472	Intermediate Similarity	NPC282508
0.8472	Intermediate Similarity	NPC471517
0.8462	Intermediate Similarity	NPC471519
0.8462	Intermediate Similarity	NPC471518
0.8456	Intermediate Similarity	NPC100482
0.8456	Intermediate Similarity	NPC277331
0.8452	Intermediate Similarity	NPC279406
0.8452	Intermediate Similarity	NPC226809
0.8442	Intermediate Similarity	NPC477612
0.8421	Intermediate Similarity	NPC215678
0.8421	Intermediate Similarity	NPC274454
0.8414	Intermediate Similarity	NPC469611
0.8411	Intermediate Similarity	NPC475492
0.8397	Intermediate Similarity	NPC224161
0.838	Intermediate Similarity	NPC145659
0.838	Intermediate Similarity	NPC9292
0.8377	Intermediate Similarity	NPC470826
0.8377	Intermediate Similarity	NPC295573
0.8377	Intermediate Similarity	NPC470098
0.8377	Intermediate Similarity	NPC473266
0.8377	Intermediate Similarity	NPC470208
0.8366	Intermediate Similarity	NPC294558
0.8366	Intermediate Similarity	NPC236202
0.8366	Intermediate Similarity	NPC58190
0.8366	Intermediate Similarity	NPC82917
0.8366	Intermediate Similarity	NPC320970
0.8366	Intermediate Similarity	NPC18185
0.8366	Intermediate Similarity	NPC263940
0.8366	Intermediate Similarity	NPC70409
0.8366	Intermediate Similarity	NPC204770
0.8366	Intermediate Similarity	NPC262297
0.8366	Intermediate Similarity	NPC328567
0.8366	Intermediate Similarity	NPC108811
0.8366	Intermediate Similarity	NPC202742
0.8366	Intermediate Similarity	NPC320671
0.8366	Intermediate Similarity	NPC327412
0.8366	Intermediate Similarity	NPC170103
0.8366	Intermediate Similarity	NPC262911
0.8356	Intermediate Similarity	NPC473665
0.8355	Intermediate Similarity	NPC181615
0.8345	Intermediate Similarity	NPC236014
0.8345	Intermediate Similarity	NPC268917
0.8345	Intermediate Similarity	NPC196765
0.8345	Intermediate Similarity	NPC164574
0.8345	Intermediate Similarity	NPC129784
0.8345	Intermediate Similarity	NPC228369
0.8345	Intermediate Similarity	NPC271945
0.8345	Intermediate Similarity	NPC118114
0.8345	Intermediate Similarity	NPC476166
0.8345	Intermediate Similarity	NPC300875
0.8345	Intermediate Similarity	NPC17343
0.8345	Intermediate Similarity	NPC181497
0.8345	Intermediate Similarity	NPC12875
0.8345	Intermediate Similarity	NPC150011
0.8345	Intermediate Similarity	NPC206224
0.8345	Intermediate Similarity	NPC129106
0.8345	Intermediate Similarity	NPC280653
0.8345	Intermediate Similarity	NPC207892
0.8344	Intermediate Similarity	NPC46335
0.8323	Intermediate Similarity	NPC118000
0.8323	Intermediate Similarity	NPC205501
0.8323	Intermediate Similarity	NPC162976
0.8323	Intermediate Similarity	NPC261896
0.8312	Intermediate Similarity	NPC329836
0.8301	Intermediate Similarity	NPC96576
0.8301	Intermediate Similarity	NPC260397
0.8301	Intermediate Similarity	NPC324492
0.8301	Intermediate Similarity	NPC317053
0.8299	Intermediate Similarity	NPC115335
0.8299	Intermediate Similarity	NPC198154
0.8299	Intermediate Similarity	NPC296915
0.8299	Intermediate Similarity	NPC97834
0.8299	Intermediate Similarity	NPC223008
0.8299	Intermediate Similarity	NPC225696
0.8288	Intermediate Similarity	NPC13005
0.8278	Intermediate Similarity	NPC277784
0.8276	Intermediate Similarity	NPC27187
0.8276	Intermediate Similarity	NPC470225
0.8269	Intermediate Similarity	NPC471403
0.8267	Intermediate Similarity	NPC221134
0.8258	Intermediate Similarity	NPC211561
0.8258	Intermediate Similarity	NPC318373
0.8258	Intermediate Similarity	NPC321657
0.8258	Intermediate Similarity	NPC476969
0.8255	Intermediate Similarity	NPC474687
0.8255	Intermediate Similarity	NPC94994
0.8219	Intermediate Similarity	NPC472590
0.8207	Intermediate Similarity	NPC93962
0.8188	Intermediate Similarity	NPC3049
0.8187	Intermediate Similarity	NPC147743
0.8187	Intermediate Similarity	NPC4809
0.8187	Intermediate Similarity	NPC73517
0.8187	Intermediate Similarity	NPC470827
0.8187	Intermediate Similarity	NPC125495
0.8182	Intermediate Similarity	NPC102280
0.8182	Intermediate Similarity	NPC155564
0.8182	Intermediate Similarity	NPC126291
0.8182	Intermediate Similarity	NPC248053
0.8182	Intermediate Similarity	NPC113495
0.817	Intermediate Similarity	NPC114119
0.817	Intermediate Similarity	NPC471415
0.817	Intermediate Similarity	NPC470097
0.8158	Intermediate Similarity	NPC186033
0.8158	Intermediate Similarity	NPC472087
0.8158	Intermediate Similarity	NPC472088
0.8153	Intermediate Similarity	NPC259707
0.8146	Intermediate Similarity	NPC472091
0.8146	Intermediate Similarity	NPC472090
0.8146	Intermediate Similarity	NPC472092
0.8138	Intermediate Similarity	NPC39064
0.8138	Intermediate Similarity	NPC47283
0.8138	Intermediate Similarity	NPC53986
0.8138	Intermediate Similarity	NPC38664
0.8138	Intermediate Similarity	NPC215300
0.8137	Intermediate Similarity	NPC205613
0.8137	Intermediate Similarity	NPC470828
0.8137	Intermediate Similarity	NPC212614
0.8137	Intermediate Similarity	NPC106601
0.8137	Intermediate Similarity	NPC151474
0.8137	Intermediate Similarity	NPC86630
0.8137	Intermediate Similarity	NPC159526
0.8137	Intermediate Similarity	NPC471404
0.8125	Intermediate Similarity	NPC262573
0.8125	Intermediate Similarity	NPC55463
0.8125	Intermediate Similarity	NPC471215
0.8125	Intermediate Similarity	NPC170485
0.8125	Intermediate Similarity	NPC166116

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 NPC218801 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	424
0.1-0.2	965
0.2-0.3	1707
0.3-0.4	2805
0.4-0.5	1685
0.5-0.6	965
0.6-0.7	521
0.7-0.8	73
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8403	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD4908	Phase 1
0.7959	Intermediate Similarity	NPD4625	Phase 3
0.7945	Intermediate Similarity	NPD2861	Phase 2
0.7902	Intermediate Similarity	NPD1610	Phase 2
0.7711	Intermediate Similarity	NPD6959	Discontinued
0.7667	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5735	Approved
0.7622	Intermediate Similarity	NPD1548	Phase 1
0.7622	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7199	Phase 2
0.7582	Intermediate Similarity	NPD6353	Approved
0.758	Intermediate Similarity	NPD3892	Phase 2
0.7566	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1613	Approved
0.7551	Intermediate Similarity	NPD4749	Approved
0.7551	Intermediate Similarity	NPD5327	Phase 3
0.7515	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7485	Intermediate Similarity	NPD7228	Approved
0.747	Intermediate Similarity	NPD4965	Approved
0.747	Intermediate Similarity	NPD4966	Approved
0.747	Intermediate Similarity	NPD7768	Phase 2
0.747	Intermediate Similarity	NPD4967	Phase 2
0.7452	Intermediate Similarity	NPD7037	Approved
0.7417	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7447	Phase 1
0.7391	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5762	Approved
0.7389	Intermediate Similarity	NPD5763	Approved
0.7353	Intermediate Similarity	NPD7229	Phase 3
0.7351	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7819	Suspended
0.7338	Intermediate Similarity	NPD4060	Phase 1
0.7338	Intermediate Similarity	NPD4140	Approved
0.7329	Intermediate Similarity	NPD7213	Phase 3
0.7329	Intermediate Similarity	NPD7212	Phase 2
0.7315	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD37	Approved
0.7267	Intermediate Similarity	NPD6696	Suspended
0.7267	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3027	Phase 3
0.725	Intermediate Similarity	NPD7466	Approved
0.7246	Intermediate Similarity	NPD8455	Phase 2
0.7244	Intermediate Similarity	NPD2157	Approved
0.7232	Intermediate Similarity	NPD8313	Approved
0.7232	Intermediate Similarity	NPD8312	Approved
0.7222	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7041	Phase 2
0.7215	Intermediate Similarity	NPD6099	Approved
0.7215	Intermediate Similarity	NPD6100	Approved
0.7188	Intermediate Similarity	NPD6674	Discontinued
0.7179	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5124	Phase 1
0.7171	Intermediate Similarity	NPD4624	Approved
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD7741	Discontinued
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7134	Intermediate Similarity	NPD4097	Suspended
0.7119	Intermediate Similarity	NPD7240	Approved
0.7115	Intermediate Similarity	NPD3620	Phase 2
0.7115	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD8127	Discontinued
0.7079	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8651	Approved
0.7037	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6273	Approved
0.7029	Intermediate Similarity	NPD7473	Discontinued
0.7027	Intermediate Similarity	NPD3091	Approved
0.7024	Intermediate Similarity	NPD7411	Suspended
0.7018	Intermediate Similarity	NPD3749	Approved
0.7018	Intermediate Similarity	NPD7833	Phase 2
0.7018	Intermediate Similarity	NPD7831	Phase 2
0.7018	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7390	Discontinued
0.7	Intermediate Similarity	NPD8053	Approved
0.7	Intermediate Similarity	NPD8054	Approved
0.6993	Remote Similarity	NPD3094	Phase 2
0.6987	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6166	Phase 2
0.6971	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4380	Phase 2
0.6957	Remote Similarity	NPD6002	Phase 3
0.6957	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6005	Phase 3
0.6957	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6004	Phase 3
0.6957	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6232	Discontinued
0.6954	Remote Similarity	NPD3092	Approved
0.6948	Remote Similarity	NPD6584	Phase 3
0.6947	Remote Similarity	NPD7680	Approved
0.6943	Remote Similarity	NPD8032	Phase 2
0.6933	Remote Similarity	NPD7003	Approved
0.6927	Remote Similarity	NPD6559	Discontinued
0.6923	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7075	Discontinued
0.6914	Remote Similarity	NPD1549	Phase 2
0.6903	Remote Similarity	NPD5736	Approved
0.6875	Remote Similarity	NPD7097	Phase 1
0.6875	Remote Similarity	NPD7119	Phase 2
0.6868	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2533	Approved
0.6867	Remote Similarity	NPD2534	Approved
0.6867	Remote Similarity	NPD2532	Approved
0.6855	Remote Similarity	NPD6355	Discontinued
0.6854	Remote Similarity	NPD8156	Discontinued
0.6854	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD422	Phase 1
0.6839	Remote Similarity	NPD5494	Approved
0.6835	Remote Similarity	NPD6663	Approved
0.6832	Remote Similarity	NPD3748	Approved
0.6832	Remote Similarity	NPD5588	Approved
0.6824	Remote Similarity	NPD6671	Approved
0.6821	Remote Similarity	NPD3095	Discontinued
0.6821	Remote Similarity	NPD4626	Approved
0.6805	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8251	Approved
0.6798	Remote Similarity	NPD8099	Discontinued
0.6798	Remote Similarity	NPD8252	Approved
0.6795	Remote Similarity	NPD3018	Phase 2
0.6793	Remote Similarity	NPD7906	Approved
0.6784	Remote Similarity	NPD1934	Approved
0.6779	Remote Similarity	NPD7340	Approved
0.6768	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7019	Approved
0.6766	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7020	Approved
0.6761	Remote Similarity	NPD3787	Discontinued
0.6759	Remote Similarity	NPD4750	Phase 3
0.6755	Remote Similarity	NPD5691	Approved
0.6753	Remote Similarity	NPD6582	Phase 2
0.6753	Remote Similarity	NPD6583	Phase 3
0.6744	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2342	Discontinued
0.6735	Remote Similarity	NPD7843	Approved
0.6728	Remote Similarity	NPD7033	Discontinued
0.6728	Remote Similarity	NPD1510	Phase 2
0.6724	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7074	Phase 3
0.6721	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4059	Approved
0.6711	Remote Similarity	NPD7157	Approved
0.6707	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD3818	Discontinued
0.6687	Remote Similarity	NPD2796	Approved
0.6687	Remote Similarity	NPD2238	Phase 2
0.6687	Remote Similarity	NPD5408	Approved
0.6687	Remote Similarity	NPD5404	Approved
0.6687	Remote Similarity	NPD5405	Approved
0.6687	Remote Similarity	NPD5406	Approved
0.6684	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD3051	Approved
0.6667	Remote Similarity	NPD7313	Approved
0.6667	Remote Similarity	NPD4536	Approved
0.6667	Remote Similarity	NPD7311	Approved
0.6667	Remote Similarity	NPD7312	Approved
0.6667	Remote Similarity	NPD4578	Approved
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD7310	Approved
0.6667	Remote Similarity	NPD7773	Phase 2
0.6667	Remote Similarity	NPD4577	Approved
0.6667	Remote Similarity	NPD4538	Approved
0.6649	Remote Similarity	NPD4663	Approved
0.6647	Remote Similarity	NPD6666	Approved
0.6647	Remote Similarity	NPD5761	Phase 2
0.6647	Remote Similarity	NPD6667	Approved
0.6647	Remote Similarity	NPD5760	Phase 2
0.6647	Remote Similarity	NPD5929	Approved
0.6647	Remote Similarity	NPD1653	Approved
0.6647	Remote Similarity	NPD5058	Phase 3
0.6646	Remote Similarity	NPD3657	Discovery
0.6645	Remote Similarity	NPD2983	Phase 2
0.6645	Remote Similarity	NPD2982	Phase 2
0.663	Remote Similarity	NPD7472	Approved
0.663	Remote Similarity	NPD7309	Approved
0.6629	Remote Similarity	NPD2970	Approved
0.6629	Remote Similarity	NPD2969	Approved
0.6627	Remote Similarity	NPD6331	Phase 2
0.6627	Remote Similarity	NPD8166	Discontinued
0.6627	Remote Similarity	NPD6090	Discontinued
0.6627	Remote Similarity	NPD4319	Phase 2

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