NPASS Compound

Structure

NPC239685 OpenBabel07101718222D 23 24 0 0 1 0 0 0 0 0999 V2000 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3660 3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 3.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6340 3.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 4 14 1 0 0 0 0 5 19 1 0 0 0 0 6 7 1 0 0 0 0 6 16 2 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 14 17 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 6 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 20 1 6 0 0 0 20 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	3.624
LogD:	2.435
LogS:	-3.785
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.734
Synthetic Accessibility Score:	4.513
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.997
MDCK Permeability:	2.7583266273722984e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.076
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.545
Plasma Protein Binding (PPB):	90.03915405273438%
Volume Distribution (VD):	0.326
Pgp-substrate:	6.511347770690918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.337
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.701
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.593
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.721

ADMET: Excretion

Clearance (CL):	2.332
Half-life (T1/2):	0.498

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.748
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.297
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.807
Carcinogencity:	0.922
Eye Corrosion:	0.015
Eye Irritation:	0.05
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC239685

Natural Product ID:	NPC239685
*Common Name:**	9R-Hydroxycallicarpic Acid A
IUPAC Name:	3-[(1S,2S,8aS)-8a-hydroxy-1-methyl-6-propan-2-yl-2-prop-1-en-2-yl-2,3,7,8-tetrahydronaphthalen-1-yl]propanoic acid
Synonyms:	9R-Hydroxycallicarpic Acid A
Standard InCHIKey:	WXVLVZIOXFNYTO-YSIASYRMSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-13(2)15-8-11-20(23)16(12-15)6-7-17(14(3)4)19(20,5)10-9-18(21)22/h6,12-13,17,23H,3,7-11H2,1-2,4-5H3,(H,21,22)/t17-,19-,20+/m0/s1
SMILES:	CC(C)C1=CC2=CC[C@@H](C(=C)C)[C@](C)(CCC(=O)O)[C@]2(CC1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL549819
PubChem CID:	25243665
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO17126	Callicarpa pilosissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19193025]
NPO17126	Callicarpa pilosissima	Species	Lamiaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	113200.0	nM	PMID[550424]

☑ 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 NPC239685 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	188
0.1-0.2	1093
0.2-0.3	4743
0.3-0.4	12686
0.4-0.5	12738
0.5-0.6	7480
0.6-0.7	3391
0.7-0.8	370
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.85	High Similarity	NPC301065
0.8315	Intermediate Similarity	NPC118011
0.8315	Intermediate Similarity	NPC36668
0.8313	Intermediate Similarity	NPC179028
0.8293	Intermediate Similarity	NPC309399
0.8256	Intermediate Similarity	NPC310470
0.8202	Intermediate Similarity	NPC72397
0.8182	Intermediate Similarity	NPC473226
0.8182	Intermediate Similarity	NPC470415
0.8152	Intermediate Similarity	NPC470958
0.8152	Intermediate Similarity	NPC470957
0.809	Intermediate Similarity	NPC231599
0.8065	Intermediate Similarity	NPC266899
0.8049	Intermediate Similarity	NPC213223
0.8046	Intermediate Similarity	NPC49019
0.8023	Intermediate Similarity	NPC473420
0.8023	Intermediate Similarity	NPC142244
0.8	Intermediate Similarity	NPC471717
0.8	Intermediate Similarity	NPC48107
0.8	Intermediate Similarity	NPC476427
0.8	Intermediate Similarity	NPC124927
0.8	Intermediate Similarity	NPC24816
0.8	Intermediate Similarity	NPC475101
0.7978	Intermediate Similarity	NPC82979
0.7957	Intermediate Similarity	NPC469406
0.7952	Intermediate Similarity	NPC476795
0.7912	Intermediate Similarity	NPC474918
0.7912	Intermediate Similarity	NPC472688
0.7912	Intermediate Similarity	NPC472676
0.7895	Intermediate Similarity	NPC189880
0.7889	Intermediate Similarity	NPC181327
0.7882	Intermediate Similarity	NPC74410
0.7882	Intermediate Similarity	NPC321514
0.7872	Intermediate Similarity	NPC134067
0.7865	Intermediate Similarity	NPC269638
0.7857	Intermediate Similarity	NPC69143
0.7841	Intermediate Similarity	NPC69279
0.7841	Intermediate Similarity	NPC83569
0.7831	Intermediate Similarity	NPC237591
0.7831	Intermediate Similarity	NPC3753
0.7831	Intermediate Similarity	NPC306928
0.7805	Intermediate Similarity	NPC160817
0.7791	Intermediate Similarity	NPC196827
0.7791	Intermediate Similarity	NPC231431
0.7791	Intermediate Similarity	NPC274996
0.7789	Intermediate Similarity	NPC173272
0.7778	Intermediate Similarity	NPC472974
0.7766	Intermediate Similarity	NPC196227
0.7766	Intermediate Similarity	NPC250075
0.7765	Intermediate Similarity	NPC97377
0.7765	Intermediate Similarity	NPC266193
0.7765	Intermediate Similarity	NPC61952
0.7765	Intermediate Similarity	NPC137547
0.7765	Intermediate Similarity	NPC257666
0.7742	Intermediate Similarity	NPC301244
0.7742	Intermediate Similarity	NPC204341
0.7742	Intermediate Similarity	NPC116726
0.7738	Intermediate Similarity	NPC279666
0.7738	Intermediate Similarity	NPC192540
0.7738	Intermediate Similarity	NPC476844
0.7727	Intermediate Similarity	NPC260956
0.7727	Intermediate Similarity	NPC73882
0.7717	Intermediate Similarity	NPC77168
0.7717	Intermediate Similarity	NPC84271
0.7717	Intermediate Similarity	NPC102414
0.7711	Intermediate Similarity	NPC35656
0.7708	Intermediate Similarity	NPC254496
0.7708	Intermediate Similarity	NPC320306
0.7708	Intermediate Similarity	NPC472851
0.7701	Intermediate Similarity	NPC37038
0.7701	Intermediate Similarity	NPC271104
0.77	Intermediate Similarity	NPC469607
0.77	Intermediate Similarity	NPC323834
0.7692	Intermediate Similarity	NPC71507
0.7692	Intermediate Similarity	NPC171722
0.7692	Intermediate Similarity	NPC471792
0.7692	Intermediate Similarity	NPC476409
0.7692	Intermediate Similarity	NPC128644
0.7684	Intermediate Similarity	NPC174948
0.7684	Intermediate Similarity	NPC173875
0.7684	Intermediate Similarity	NPC473240
0.7684	Intermediate Similarity	NPC48330
0.7684	Intermediate Similarity	NPC469995
0.7684	Intermediate Similarity	NPC53565
0.7684	Intermediate Similarity	NPC318282
0.7677	Intermediate Similarity	NPC230918
0.7674	Intermediate Similarity	NPC198240
0.7674	Intermediate Similarity	NPC169095
0.7674	Intermediate Similarity	NPC239098
0.7674	Intermediate Similarity	NPC471409
0.7674	Intermediate Similarity	NPC275494
0.767	Intermediate Similarity	NPC188738
0.7667	Intermediate Similarity	NPC15807
0.766	Intermediate Similarity	NPC477855
0.7653	Intermediate Similarity	NPC146822
0.7653	Intermediate Similarity	NPC472924
0.7647	Intermediate Similarity	NPC151622
0.7647	Intermediate Similarity	NPC7629
0.7647	Intermediate Similarity	NPC180886
0.7647	Intermediate Similarity	NPC472305
0.7647	Intermediate Similarity	NPC899
0.764	Intermediate Similarity	NPC70834
0.764	Intermediate Similarity	NPC107253
0.764	Intermediate Similarity	NPC102197
0.764	Intermediate Similarity	NPC105173
0.764	Intermediate Similarity	NPC97913
0.7634	Intermediate Similarity	NPC469400
0.7629	Intermediate Similarity	NPC186810
0.7629	Intermediate Similarity	NPC48647
0.7624	Intermediate Similarity	NPC472925
0.7619	Intermediate Similarity	NPC476046
0.7619	Intermediate Similarity	NPC103958
0.7619	Intermediate Similarity	NPC183503
0.7619	Intermediate Similarity	NPC161923
0.7619	Intermediate Similarity	NPC18819
0.7619	Intermediate Similarity	NPC251970
0.7619	Intermediate Similarity	NPC283908
0.7619	Intermediate Similarity	NPC46610
0.7619	Intermediate Similarity	NPC241854
0.7614	Intermediate Similarity	NPC470298
0.7614	Intermediate Similarity	NPC38350
0.7614	Intermediate Similarity	NPC327002
0.7614	Intermediate Similarity	NPC201912
0.7614	Intermediate Similarity	NPC221647
0.7604	Intermediate Similarity	NPC29952
0.7604	Intermediate Similarity	NPC476327
0.7604	Intermediate Similarity	NPC477853
0.7604	Intermediate Similarity	NPC328371
0.7604	Intermediate Similarity	NPC476318
0.76	Intermediate Similarity	NPC477812
0.7586	Intermediate Similarity	NPC477371
0.7586	Intermediate Similarity	NPC199595
0.7582	Intermediate Similarity	NPC472985
0.7582	Intermediate Similarity	NPC73038
0.7582	Intermediate Similarity	NPC322159
0.7582	Intermediate Similarity	NPC472869
0.7582	Intermediate Similarity	NPC472986
0.7579	Intermediate Similarity	NPC80365
0.7576	Intermediate Similarity	NPC235369
0.7573	Intermediate Similarity	NPC286880
0.7558	Intermediate Similarity	NPC107039
0.7558	Intermediate Similarity	NPC471899
0.7558	Intermediate Similarity	NPC34110
0.7558	Intermediate Similarity	NPC132542
0.7558	Intermediate Similarity	NPC471897
0.7558	Intermediate Similarity	NPC165711
0.7556	Intermediate Similarity	NPC165064
0.7556	Intermediate Similarity	NPC164577
0.7556	Intermediate Similarity	NPC472865
0.7556	Intermediate Similarity	NPC295799
0.7553	Intermediate Similarity	NPC45269
0.7551	Intermediate Similarity	NPC471413
0.7551	Intermediate Similarity	NPC472972
0.7551	Intermediate Similarity	NPC327431
0.7551	Intermediate Similarity	NPC241221
0.7529	Intermediate Similarity	NPC39362
0.7528	Intermediate Similarity	NPC69101
0.7528	Intermediate Similarity	NPC92226
0.7528	Intermediate Similarity	NPC296367
0.7528	Intermediate Similarity	NPC251779
0.7527	Intermediate Similarity	NPC314727
0.7527	Intermediate Similarity	NPC214387
0.7527	Intermediate Similarity	NPC95246
0.7527	Intermediate Similarity	NPC472973
0.7527	Intermediate Similarity	NPC474972
0.7527	Intermediate Similarity	NPC118193
0.7527	Intermediate Similarity	NPC161751
0.7527	Intermediate Similarity	NPC256902
0.7527	Intermediate Similarity	NPC474686
0.7526	Intermediate Similarity	NPC170131
0.7526	Intermediate Similarity	NPC99726
0.7526	Intermediate Similarity	NPC161147
0.7526	Intermediate Similarity	NPC285513
0.7524	Intermediate Similarity	NPC471204
0.75	Intermediate Similarity	NPC109576
0.75	Intermediate Similarity	NPC179798
0.75	Intermediate Similarity	NPC233836
0.75	Intermediate Similarity	NPC56747
0.75	Intermediate Similarity	NPC136948
0.75	Intermediate Similarity	NPC272617
0.75	Intermediate Similarity	NPC259286
0.75	Intermediate Similarity	NPC304180
0.75	Intermediate Similarity	NPC26139
0.75	Intermediate Similarity	NPC187376
0.75	Intermediate Similarity	NPC159046
0.75	Intermediate Similarity	NPC180015
0.75	Intermediate Similarity	NPC130016
0.75	Intermediate Similarity	NPC90177
0.75	Intermediate Similarity	NPC298904
0.75	Intermediate Similarity	NPC312561
0.7475	Intermediate Similarity	NPC163372
0.7475	Intermediate Similarity	NPC302537
0.7475	Intermediate Similarity	NPC81530
0.7475	Intermediate Similarity	NPC471412
0.7474	Intermediate Similarity	NPC69454
0.7474	Intermediate Similarity	NPC131840
0.7474	Intermediate Similarity	NPC206810
0.7473	Intermediate Similarity	NPC52628
0.7473	Intermediate Similarity	NPC147921
0.7473	Intermediate Similarity	NPC109528

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 NPC239685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1622
0.2-0.3	3682
0.3-0.4	2365
0.4-0.5	832
0.5-0.6	368
0.6-0.7	81
0.7-0.8	8
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7849	Intermediate Similarity	NPD5779	Approved
0.7849	Intermediate Similarity	NPD5778	Approved
0.7368	Intermediate Similarity	NPD5284	Approved
0.7368	Intermediate Similarity	NPD6411	Approved
0.7368	Intermediate Similarity	NPD5281	Approved
0.734	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3573	Approved
0.7204	Intermediate Similarity	NPD4694	Approved
0.7204	Intermediate Similarity	NPD5280	Approved
0.7204	Intermediate Similarity	NPD4623	Approved
0.7204	Intermediate Similarity	NPD4519	Discontinued
0.7158	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD3667	Approved
0.703	Intermediate Similarity	NPD6404	Discontinued
0.701	Intermediate Similarity	NPD7515	Phase 2
0.6989	Remote Similarity	NPD4786	Approved
0.6979	Remote Similarity	NPD5328	Approved
0.6957	Remote Similarity	NPD4223	Phase 3
0.6957	Remote Similarity	NPD4221	Approved
0.6939	Remote Similarity	NPD6399	Phase 3
0.6932	Remote Similarity	NPD8264	Approved
0.6923	Remote Similarity	NPD4695	Discontinued
0.6915	Remote Similarity	NPD1696	Phase 3
0.6907	Remote Similarity	NPD5207	Approved
0.6907	Remote Similarity	NPD5692	Phase 3
0.6875	Remote Similarity	NPD4518	Approved
0.6869	Remote Similarity	NPD7748	Approved
0.6863	Remote Similarity	NPD7640	Approved
0.6863	Remote Similarity	NPD7639	Approved
0.6842	Remote Similarity	NPD5690	Phase 2
0.6842	Remote Similarity	NPD5279	Phase 3
0.6842	Remote Similarity	NPD3618	Phase 1
0.6837	Remote Similarity	NPD6050	Approved
0.6837	Remote Similarity	NPD5694	Approved
0.6837	Remote Similarity	NPD6079	Approved
0.6809	Remote Similarity	NPD4197	Approved
0.68	Remote Similarity	NPD5695	Phase 3
0.6786	Remote Similarity	NPD7331	Phase 2
0.6765	Remote Similarity	NPD7638	Approved
0.6742	Remote Similarity	NPD8039	Approved
0.6737	Remote Similarity	NPD5329	Approved
0.6735	Remote Similarity	NPD4096	Approved
0.6731	Remote Similarity	NPD5211	Phase 2
0.6698	Remote Similarity	NPD6675	Approved
0.6698	Remote Similarity	NPD6008	Approved
0.6698	Remote Similarity	NPD7128	Approved
0.6698	Remote Similarity	NPD6402	Approved
0.6698	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6098	Approved
0.6636	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD5697	Approved
0.6632	Remote Similarity	NPD3665	Phase 1
0.6632	Remote Similarity	NPD3666	Approved
0.6632	Remote Similarity	NPD3668	Phase 3
0.6632	Remote Similarity	NPD3133	Approved
0.6604	Remote Similarity	NPD5141	Approved
0.66	Remote Similarity	NPD5133	Approved
0.66	Remote Similarity	NPD4202	Approved
0.6598	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4632	Approved
0.6574	Remote Similarity	NPD6011	Approved
0.6574	Remote Similarity	NPD7320	Approved
0.6574	Remote Similarity	NPD6899	Approved
0.6574	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD5222	Approved
0.6569	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7614	Phase 1
0.6569	Remote Similarity	NPD4697	Phase 3
0.6569	Remote Similarity	NPD5221	Approved
0.6569	Remote Similarity	NPD7839	Suspended
0.6562	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6931	Approved
0.6559	Remote Similarity	NPD6930	Phase 2
0.6538	Remote Similarity	NPD5286	Approved
0.6538	Remote Similarity	NPD4700	Approved
0.6538	Remote Similarity	NPD5285	Approved
0.6538	Remote Similarity	NPD4696	Approved
0.6531	Remote Similarity	NPD5208	Approved
0.6522	Remote Similarity	NPD3617	Approved
0.6522	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6372	Approved
0.6514	Remote Similarity	NPD6013	Approved
0.6514	Remote Similarity	NPD6012	Approved
0.6514	Remote Similarity	NPD6373	Approved
0.6514	Remote Similarity	NPD6014	Approved
0.6506	Remote Similarity	NPD4192	Approved
0.6506	Remote Similarity	NPD4194	Approved
0.6506	Remote Similarity	NPD4193	Approved
0.6506	Remote Similarity	NPD4191	Approved
0.6505	Remote Similarity	NPD6084	Phase 2
0.6505	Remote Similarity	NPD5173	Approved
0.6505	Remote Similarity	NPD6083	Phase 2
0.65	Remote Similarity	NPD5693	Phase 1
0.6495	Remote Similarity	NPD6409	Approved
0.6495	Remote Similarity	NPD7334	Approved
0.6495	Remote Similarity	NPD5330	Approved
0.6495	Remote Similarity	NPD6684	Approved
0.6495	Remote Similarity	NPD7521	Approved
0.6495	Remote Similarity	NPD7146	Approved
0.6486	Remote Similarity	NPD6053	Discontinued
0.6476	Remote Similarity	NPD5223	Approved
0.6471	Remote Similarity	NPD5654	Approved
0.6465	Remote Similarity	NPD4753	Phase 2
0.6465	Remote Similarity	NPD6904	Approved
0.6465	Remote Similarity	NPD6673	Approved
0.6465	Remote Similarity	NPD6080	Approved
0.6455	Remote Similarity	NPD6883	Approved
0.6455	Remote Similarity	NPD7290	Approved
0.6455	Remote Similarity	NPD7102	Approved
0.6452	Remote Similarity	NPD6929	Approved
0.6444	Remote Similarity	NPD5733	Approved
0.6444	Remote Similarity	NPD4687	Approved
0.6442	Remote Similarity	NPD4225	Approved
0.6442	Remote Similarity	NPD5696	Approved
0.6415	Remote Similarity	NPD4633	Approved
0.6415	Remote Similarity	NPD5224	Approved
0.6415	Remote Similarity	NPD5225	Approved
0.6415	Remote Similarity	NPD5226	Approved
0.6413	Remote Similarity	NPD4756	Discovery
0.6404	Remote Similarity	NPD6009	Approved
0.6404	Remote Similarity	NPD7115	Discovery
0.6404	Remote Similarity	NPD5276	Approved
0.6396	Remote Similarity	NPD6869	Approved
0.6396	Remote Similarity	NPD6650	Approved
0.6396	Remote Similarity	NPD6649	Approved
0.6396	Remote Similarity	NPD6617	Approved
0.6396	Remote Similarity	NPD8130	Phase 1
0.6396	Remote Similarity	NPD6847	Approved
0.6396	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD1694	Approved
0.6383	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7514	Phase 3
0.6383	Remote Similarity	NPD7332	Phase 2
0.6373	Remote Similarity	NPD6001	Approved
0.6373	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7900	Approved
0.6364	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6672	Approved
0.6364	Remote Similarity	NPD5737	Approved
0.6364	Remote Similarity	NPD6903	Approved
0.6355	Remote Similarity	NPD5174	Approved
0.6355	Remote Similarity	NPD4754	Approved
0.6355	Remote Similarity	NPD5175	Approved
0.6354	Remote Similarity	NPD6695	Phase 3
0.6354	Remote Similarity	NPD5362	Discontinued
0.6346	Remote Similarity	NPD5959	Approved
0.6339	Remote Similarity	NPD6882	Approved
0.6339	Remote Similarity	NPD8297	Approved
0.6327	Remote Similarity	NPD5786	Approved
0.6325	Remote Similarity	NPD8513	Phase 3
0.6325	Remote Similarity	NPD8516	Approved
0.6325	Remote Similarity	NPD8517	Approved
0.6325	Remote Similarity	NPD8515	Approved
0.6322	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4634	Approved
0.6304	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4195	Approved
0.6264	Remote Similarity	NPD6926	Approved
0.6264	Remote Similarity	NPD6924	Approved
0.6264	Remote Similarity	NPD4058	Approved
0.6264	Remote Similarity	NPD4785	Approved
0.6264	Remote Similarity	NPD4784	Approved
0.6262	Remote Similarity	NPD7632	Discontinued
0.626	Remote Similarity	NPD7260	Phase 2
0.625	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD4270	Approved
0.6239	Remote Similarity	NPD4768	Approved
0.6239	Remote Similarity	NPD6319	Approved
0.6239	Remote Similarity	NPD4767	Approved
0.6237	Remote Similarity	NPD6925	Approved
0.6237	Remote Similarity	NPD5776	Phase 2
0.6224	Remote Similarity	NPD6893	Approved
0.6222	Remote Similarity	NPD4243	Approved
0.6211	Remote Similarity	NPD4821	Approved
0.6211	Remote Similarity	NPD4822	Approved
0.6211	Remote Similarity	NPD4820	Approved
0.6211	Remote Similarity	NPD4819	Approved
0.6196	Remote Similarity	NPD6942	Approved
0.6196	Remote Similarity	NPD7339	Approved
0.6186	Remote Similarity	NPD7154	Phase 3

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