NPASS Compound

Structure

CID289213 OpenBabel06191716092D 35 38 0 0 1 0 0 0 0 0999 V2000 -3.3826 2.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2586 2.4577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7639 -5.2038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9746 -5.7769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5366 -0.5244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2732 -3.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8460 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 1.9522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6702 -4.1193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6903 -0.9753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6909 -0.9763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2269 0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3818 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6900 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8452 -1.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -2.4391 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8460 -1.4637 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6912 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 0.4879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5372 1.4638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2272 1.4633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0971 -4.9085 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8163 -2.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3823 1.9518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8730 -4.8068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5369 0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9758 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 -5.0934 1.9631 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4941 -5.7995 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2133 -3.4317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3894 -1.7515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2699 -3.9159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 11 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 29 1 0 0 0 0 18 8 1 6 0 0 0 18 19 1 0 0 0 0 18 25 1 0 0 0 0 19 29 1 6 0 0 0 20 21 2 0 0 0 0 20 28 1 0 0 0 0 21 30 1 0 0 0 0 22 26 1 0 0 0 0 22 28 1 6 0 0 0 23 26 1 0 0 0 0 23 31 2 0 0 0 0 24 27 1 0 0 0 0 24 32 1 6 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 27 35 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.35
Volume:	529.252
LogP:	3.738
LogD:	3.076
LogS:	-3.905
# Rotatable Bonds:	6
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.404
Synthetic Accessibility Score:	4.841
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.361
MDCK Permeability:	1.2102331311325543e-05
Pgp-inhibitor:	0.697
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.346
Plasma Protein Binding (PPB):	89.57535552978516%
Volume Distribution (VD):	0.832
Pgp-substrate:	2.8117566108703613%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.494
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.943
CYP2C9-inhibitor:	0.121
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.344
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.126

ADMET: Excretion

Clearance (CL):	4.119
Half-life (T1/2):	0.683

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.182
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.052
Carcinogencity:	0.093
Eye Corrosion:	0.004
Eye Irritation:	0.029
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC289213

Natural Product ID:	NPC289213
*Common Name:**	Fomitopinic Acid A
IUPAC Name:	(2R,5S)-5,6-dihydroxy-6-methyl-2-[(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]heptanoic acid
Synonyms:
Standard InCHIKey:	GCGLPSVDVGXRFN-AMKDLFIQSA-N
Standard InCHI:	InChI=1S/C30H48O5/c1-26(2)22-10-9-21-20(28(22,5)15-14-23(26)31)13-17-29(6)19(12-16-30(21,29)7)18(25(33)34)8-11-24(32)27(3,4)35/h18-19,22,24,32,35H,8-17H2,1-7H3,(H,33,34)/t18-,19-,22+,24+,28-,29-,30+/m1/s1
SMILES:	CC1(C)[C@@H]2CCC3=C(CC[C@]4(C)[C@H](CC[C@@]34C)[C@@H](CC[C@@H](C(C)(C)O)O)C(=O)O)[C@@]2(C)CCC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481045
PubChem CID:	11363812
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15679320]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	fruit bodies	Tokushima, Japan	1999-Autumn	PMID[15679320]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	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	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	18.1	%	PMID[557449]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	1150.0	nM	PMID[557449]

☑ 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 NPC289213 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	182
0.1-0.2	1421
0.2-0.3	5716
0.3-0.4	14435
0.4-0.5	7326
0.5-0.6	6164
0.6-0.7	6003
0.7-0.8	1253
0.8-0.85	164
0.85-0.9	30
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9101	High Similarity	NPC206810
0.9091	High Similarity	NPC136801
0.8901	High Similarity	NPC200702
0.8778	High Similarity	NPC107690
0.875	High Similarity	NPC99909
0.875	High Similarity	NPC138756
0.8723	High Similarity	NPC316964
0.8696	High Similarity	NPC48330
0.8681	High Similarity	NPC470254
0.8681	High Similarity	NPC25750
0.866	High Similarity	NPC323834
0.8652	High Similarity	NPC44181
0.8636	High Similarity	NPC89077
0.8602	High Similarity	NPC173272
0.8602	High Similarity	NPC42042
0.8587	High Similarity	NPC184870
0.8587	High Similarity	NPC166906
0.8556	High Similarity	NPC476733
0.8556	High Similarity	NPC215029
0.8556	High Similarity	NPC54689
0.8539	High Similarity	NPC90652
0.8526	High Similarity	NPC167974
0.8495	Intermediate Similarity	NPC470016
0.8495	Intermediate Similarity	NPC317586
0.8495	Intermediate Similarity	NPC241156
0.8495	Intermediate Similarity	NPC173875
0.8495	Intermediate Similarity	NPC174948
0.8495	Intermediate Similarity	NPC469995
0.8495	Intermediate Similarity	NPC255809
0.8495	Intermediate Similarity	NPC318282
0.8495	Intermediate Similarity	NPC37646
0.8478	Intermediate Similarity	NPC243866
0.8462	Intermediate Similarity	NPC469400
0.8462	Intermediate Similarity	NPC20388
0.8444	Intermediate Similarity	NPC470417
0.8444	Intermediate Similarity	NPC242864
0.8438	Intermediate Similarity	NPC472924
0.8427	Intermediate Similarity	NPC55309
0.8427	Intermediate Similarity	NPC28252
0.8409	Intermediate Similarity	NPC109512
0.8404	Intermediate Similarity	NPC305483
0.8404	Intermediate Similarity	NPC95565
0.8404	Intermediate Similarity	NPC125622
0.8404	Intermediate Similarity	NPC328371
0.8404	Intermediate Similarity	NPC40765
0.8404	Intermediate Similarity	NPC96859
0.8404	Intermediate Similarity	NPC328162
0.8404	Intermediate Similarity	NPC243525
0.8404	Intermediate Similarity	NPC3772
0.8404	Intermediate Similarity	NPC7124
0.837	Intermediate Similarity	NPC189520
0.837	Intermediate Similarity	NPC150383
0.8367	Intermediate Similarity	NPC255309
0.8367	Intermediate Similarity	NPC471293
0.8367	Intermediate Similarity	NPC477812
0.8352	Intermediate Similarity	NPC32830
0.8351	Intermediate Similarity	NPC473928
0.8333	Intermediate Similarity	NPC187376
0.8333	Intermediate Similarity	NPC218383
0.8333	Intermediate Similarity	NPC159046
0.8333	Intermediate Similarity	NPC233836
0.8333	Intermediate Similarity	NPC96496
0.8316	Intermediate Similarity	NPC122294
0.8316	Intermediate Similarity	NPC320306
0.8316	Intermediate Similarity	NPC106557
0.8316	Intermediate Similarity	NPC121339
0.8316	Intermediate Similarity	NPC18319
0.8316	Intermediate Similarity	NPC43747
0.8315	Intermediate Similarity	NPC473038
0.8295	Intermediate Similarity	NPC86370
0.8283	Intermediate Similarity	NPC96377
0.828	Intermediate Similarity	NPC66429
0.828	Intermediate Similarity	NPC477855
0.828	Intermediate Similarity	NPC152897
0.8276	Intermediate Similarity	NPC201912
0.8276	Intermediate Similarity	NPC38350
0.8265	Intermediate Similarity	NPC55872
0.8265	Intermediate Similarity	NPC251017
0.8261	Intermediate Similarity	NPC219495
0.8247	Intermediate Similarity	NPC302537
0.8247	Intermediate Similarity	NPC163372
0.8242	Intermediate Similarity	NPC131470
0.8242	Intermediate Similarity	NPC143767
0.8229	Intermediate Similarity	NPC10364
0.8229	Intermediate Similarity	NPC114274
0.8229	Intermediate Similarity	NPC477854
0.8229	Intermediate Similarity	NPC197386
0.8229	Intermediate Similarity	NPC16021
0.8222	Intermediate Similarity	NPC473168
0.8222	Intermediate Similarity	NPC212843
0.8222	Intermediate Similarity	NPC155011
0.8211	Intermediate Similarity	NPC49371
0.8211	Intermediate Similarity	NPC155676
0.8211	Intermediate Similarity	NPC477853
0.8202	Intermediate Similarity	NPC165064
0.8202	Intermediate Similarity	NPC473246
0.82	Intermediate Similarity	NPC59530
0.82	Intermediate Similarity	NPC473037
0.8191	Intermediate Similarity	NPC470958
0.8191	Intermediate Similarity	NPC318332
0.8191	Intermediate Similarity	NPC240617
0.8191	Intermediate Similarity	NPC470957
0.8182	Intermediate Similarity	NPC28656
0.8182	Intermediate Similarity	NPC260956
0.8172	Intermediate Similarity	NPC297265
0.8172	Intermediate Similarity	NPC154101
0.8172	Intermediate Similarity	NPC23434
0.8172	Intermediate Similarity	NPC19114
0.8163	Intermediate Similarity	NPC119601
0.8163	Intermediate Similarity	NPC308726
0.8152	Intermediate Similarity	NPC275740
0.8152	Intermediate Similarity	NPC474889
0.8152	Intermediate Similarity	NPC186688
0.8152	Intermediate Similarity	NPC84271
0.8152	Intermediate Similarity	NPC102414
0.8152	Intermediate Similarity	NPC475921
0.8152	Intermediate Similarity	NPC155479
0.8152	Intermediate Similarity	NPC77168
0.8152	Intermediate Similarity	NPC214387
0.8152	Intermediate Similarity	NPC86319
0.8152	Intermediate Similarity	NPC474704
0.8144	Intermediate Similarity	NPC474720
0.8144	Intermediate Similarity	NPC88198
0.8144	Intermediate Similarity	NPC205899
0.8144	Intermediate Similarity	NPC157787
0.8144	Intermediate Similarity	NPC51370
0.8144	Intermediate Similarity	NPC144660
0.8144	Intermediate Similarity	NPC327431
0.8144	Intermediate Similarity	NPC307954
0.8144	Intermediate Similarity	NPC299971
0.8144	Intermediate Similarity	NPC287833
0.8132	Intermediate Similarity	NPC474684
0.8132	Intermediate Similarity	NPC312215
0.8132	Intermediate Similarity	NPC142361
0.8125	Intermediate Similarity	NPC108078
0.8111	Intermediate Similarity	NPC474083
0.8105	Intermediate Similarity	NPC469599
0.8105	Intermediate Similarity	NPC263347
0.8105	Intermediate Similarity	NPC127063
0.8105	Intermediate Similarity	NPC279974
0.81	Intermediate Similarity	NPC196528
0.81	Intermediate Similarity	NPC51452
0.809	Intermediate Similarity	NPC83569
0.809	Intermediate Similarity	NPC278648
0.809	Intermediate Similarity	NPC476082
0.809	Intermediate Similarity	NPC477373
0.809	Intermediate Similarity	NPC69279
0.809	Intermediate Similarity	NPC470015
0.809	Intermediate Similarity	NPC168188
0.8085	Intermediate Similarity	NPC224060
0.8085	Intermediate Similarity	NPC244356
0.8085	Intermediate Similarity	NPC472930
0.8081	Intermediate Similarity	NPC191892
0.8081	Intermediate Similarity	NPC55954
0.8081	Intermediate Similarity	NPC140723
0.8081	Intermediate Similarity	NPC117185
0.8081	Intermediate Similarity	NPC218513
0.8068	Intermediate Similarity	NPC147066
0.8065	Intermediate Similarity	NPC111585
0.8065	Intermediate Similarity	NPC477149
0.8065	Intermediate Similarity	NPC183283
0.8065	Intermediate Similarity	NPC477147
0.8065	Intermediate Similarity	NPC175628
0.8065	Intermediate Similarity	NPC148414
0.8046	Intermediate Similarity	NPC477371
0.8043	Intermediate Similarity	NPC229407
0.8043	Intermediate Similarity	NPC254572
0.8043	Intermediate Similarity	NPC250687
0.8043	Intermediate Similarity	NPC183546
0.8043	Intermediate Similarity	NPC53911
0.8043	Intermediate Similarity	NPC294480
0.8043	Intermediate Similarity	NPC48824
0.8043	Intermediate Similarity	NPC255176
0.8043	Intermediate Similarity	NPC193360
0.8041	Intermediate Similarity	NPC471717
0.8039	Intermediate Similarity	NPC304495
0.8022	Intermediate Similarity	NPC475007
0.8022	Intermediate Similarity	NPC72133
0.8022	Intermediate Similarity	NPC324063
0.8022	Intermediate Similarity	NPC56588
0.8021	Intermediate Similarity	NPC249954
0.8021	Intermediate Similarity	NPC471463
0.8021	Intermediate Similarity	NPC472941
0.8021	Intermediate Similarity	NPC456
0.802	Intermediate Similarity	NPC43285
0.802	Intermediate Similarity	NPC472925
0.802	Intermediate Similarity	NPC58370
0.8	Intermediate Similarity	NPC221758
0.8	Intermediate Similarity	NPC209502
0.8	Intermediate Similarity	NPC85774
0.8	Intermediate Similarity	NPC223741
0.8	Intermediate Similarity	NPC473898
0.8	Intermediate Similarity	NPC59453
0.8	Intermediate Similarity	NPC174051
0.8	Intermediate Similarity	NPC67831
0.8	Intermediate Similarity	NPC96268
0.8	Intermediate Similarity	NPC209882
0.8	Intermediate Similarity	NPC82902
0.8	Intermediate Similarity	NPC469406
0.8	Intermediate Similarity	NPC204833

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 NPC289213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1948
0.2-0.3	4052
0.3-0.4	1981
0.4-0.5	540
0.5-0.6	167
0.6-0.7	200
0.7-0.8	103
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD4786	Approved
0.7957	Intermediate Similarity	NPD5328	Approved
0.7895	Intermediate Similarity	NPD6399	Phase 3
0.7789	Intermediate Similarity	NPD6079	Approved
0.7778	Intermediate Similarity	NPD3667	Approved
0.7755	Intermediate Similarity	NPD6084	Phase 2
0.7755	Intermediate Similarity	NPD6083	Phase 2
0.7745	Intermediate Similarity	NPD6402	Approved
0.7745	Intermediate Similarity	NPD5739	Approved
0.7745	Intermediate Similarity	NPD7128	Approved
0.7745	Intermediate Similarity	NPD6675	Approved
0.7736	Intermediate Similarity	NPD4632	Approved
0.7732	Intermediate Similarity	NPD5695	Phase 3
0.7667	Intermediate Similarity	NPD4692	Approved
0.7667	Intermediate Similarity	NPD4139	Approved
0.7634	Intermediate Similarity	NPD5279	Phase 3
0.7609	Intermediate Similarity	NPD3665	Phase 1
0.7609	Intermediate Similarity	NPD3666	Approved
0.7609	Intermediate Similarity	NPD3133	Approved
0.7604	Intermediate Similarity	NPD5284	Approved
0.7604	Intermediate Similarity	NPD5281	Approved
0.7596	Intermediate Similarity	NPD6881	Approved
0.7596	Intermediate Similarity	NPD7320	Approved
0.7596	Intermediate Similarity	NPD6899	Approved
0.7579	Intermediate Similarity	NPD4753	Phase 2
0.7576	Intermediate Similarity	NPD4755	Approved
0.7528	Intermediate Similarity	NPD6697	Approved
0.7528	Intermediate Similarity	NPD6115	Approved
0.7528	Intermediate Similarity	NPD6114	Approved
0.7528	Intermediate Similarity	NPD6118	Approved
0.7527	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD6372	Approved
0.7524	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD5701	Approved
0.75	Intermediate Similarity	NPD5697	Approved
0.7477	Intermediate Similarity	NPD8297	Approved
0.7475	Intermediate Similarity	NPD5221	Approved
0.7475	Intermediate Similarity	NPD5222	Approved
0.7475	Intermediate Similarity	NPD4697	Phase 3
0.7475	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD5737	Approved
0.7474	Intermediate Similarity	NPD6672	Approved
0.7453	Intermediate Similarity	NPD4634	Approved
0.7453	Intermediate Similarity	NPD7102	Approved
0.7453	Intermediate Similarity	NPD6883	Approved
0.7453	Intermediate Similarity	NPD7290	Approved
0.7447	Intermediate Similarity	NPD3618	Phase 1
0.7447	Intermediate Similarity	NPD6684	Approved
0.7447	Intermediate Similarity	NPD7146	Approved
0.7447	Intermediate Similarity	NPD7334	Approved
0.7447	Intermediate Similarity	NPD6409	Approved
0.7447	Intermediate Similarity	NPD5330	Approved
0.7447	Intermediate Similarity	NPD7521	Approved
0.7429	Intermediate Similarity	NPD6011	Approved
0.7426	Intermediate Similarity	NPD4696	Approved
0.7426	Intermediate Similarity	NPD4700	Approved
0.7426	Intermediate Similarity	NPD5285	Approved
0.7426	Intermediate Similarity	NPD5286	Approved
0.7423	Intermediate Similarity	NPD7515	Phase 2
0.74	Intermediate Similarity	NPD5173	Approved
0.7391	Intermediate Similarity	NPD4221	Approved
0.7391	Intermediate Similarity	NPD4223	Phase 3
0.7383	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6847	Approved
0.7383	Intermediate Similarity	NPD6617	Approved
0.7383	Intermediate Similarity	NPD6649	Approved
0.7383	Intermediate Similarity	NPD6869	Approved
0.7383	Intermediate Similarity	NPD8130	Phase 1
0.7383	Intermediate Similarity	NPD6650	Approved
0.7364	Intermediate Similarity	NPD6009	Approved
0.7358	Intermediate Similarity	NPD6012	Approved
0.7358	Intermediate Similarity	NPD6013	Approved
0.7358	Intermediate Similarity	NPD6014	Approved
0.7353	Intermediate Similarity	NPD5223	Approved
0.7347	Intermediate Similarity	NPD4202	Approved
0.734	Intermediate Similarity	NPD5329	Approved
0.7333	Intermediate Similarity	NPD3617	Approved
0.7333	Intermediate Similarity	NPD6412	Phase 2
0.7327	Intermediate Similarity	NPD5696	Approved
0.7321	Intermediate Similarity	NPD6319	Approved
0.7315	Intermediate Similarity	NPD6882	Approved
0.7312	Intermediate Similarity	NPD4788	Approved
0.7303	Intermediate Similarity	NPD6117	Approved
0.7292	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6903	Approved
0.7282	Intermediate Similarity	NPD5211	Phase 2
0.7282	Intermediate Similarity	NPD4633	Approved
0.7282	Intermediate Similarity	NPD5224	Approved
0.7282	Intermediate Similarity	NPD5225	Approved
0.7282	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5690	Phase 2
0.7263	Intermediate Similarity	NPD5280	Approved
0.7263	Intermediate Similarity	NPD4694	Approved
0.7263	Intermediate Similarity	NPD6098	Approved
0.7245	Intermediate Similarity	NPD6411	Approved
0.7245	Intermediate Similarity	NPD6050	Approved
0.7238	Intermediate Similarity	NPD6008	Approved
0.7234	Intermediate Similarity	NPD3668	Phase 3
0.7234	Intermediate Similarity	NPD4197	Approved
0.7222	Intermediate Similarity	NPD6116	Phase 1
0.7216	Intermediate Similarity	NPD6080	Approved
0.7216	Intermediate Similarity	NPD6904	Approved
0.7216	Intermediate Similarity	NPD6673	Approved
0.7212	Intermediate Similarity	NPD4754	Approved
0.7212	Intermediate Similarity	NPD5175	Approved
0.7212	Intermediate Similarity	NPD5174	Approved
0.72	Intermediate Similarity	NPD4629	Approved
0.72	Intermediate Similarity	NPD5210	Approved
0.7196	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD3703	Phase 2
0.7157	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.7143	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5141	Approved
0.713	Intermediate Similarity	NPD7604	Phase 2
0.7105	Intermediate Similarity	NPD5983	Phase 2
0.71	Intermediate Similarity	NPD7748	Approved
0.7087	Intermediate Similarity	NPD7639	Approved
0.7087	Intermediate Similarity	NPD7640	Approved
0.7083	Intermediate Similarity	NPD4693	Phase 3
0.7083	Intermediate Similarity	NPD4689	Approved
0.7083	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4688	Approved
0.7083	Intermediate Similarity	NPD5205	Approved
0.7083	Intermediate Similarity	NPD4138	Approved
0.7083	Intermediate Similarity	NPD4690	Approved
0.7075	Intermediate Similarity	NPD4768	Approved
0.7075	Intermediate Similarity	NPD4767	Approved
0.7071	Intermediate Similarity	NPD8035	Phase 2
0.7071	Intermediate Similarity	NPD8034	Phase 2
0.7071	Intermediate Similarity	NPD5694	Approved
0.7069	Intermediate Similarity	NPD7492	Approved
0.7054	Intermediate Similarity	NPD7115	Discovery
0.7045	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6081	Approved
0.7045	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6101	Approved
0.7037	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6059	Approved
0.7018	Intermediate Similarity	NPD6054	Approved
0.7009	Intermediate Similarity	NPD6336	Discontinued
0.7009	Intermediate Similarity	NPD6616	Approved
0.7	Intermediate Similarity	NPD5779	Approved
0.7	Intermediate Similarity	NPD5778	Approved
0.7	Intermediate Similarity	NPD6942	Approved
0.7	Intermediate Similarity	NPD7339	Approved
0.7	Intermediate Similarity	NPD3702	Approved
0.7	Intermediate Similarity	NPD6053	Discontinued
0.6991	Remote Similarity	NPD6335	Approved
0.6989	Remote Similarity	NPD5368	Approved
0.6989	Remote Similarity	NPD7525	Registered
0.6989	Remote Similarity	NPD4748	Discontinued
0.697	Remote Similarity	NPD5207	Approved
0.6964	Remote Similarity	NPD6868	Approved
0.6964	Remote Similarity	NPD6274	Approved
0.6952	Remote Similarity	NPD7632	Discontinued
0.6949	Remote Similarity	NPD7078	Approved
0.6949	Remote Similarity	NPD8293	Discontinued
0.6944	Remote Similarity	NPD5128	Approved
0.6944	Remote Similarity	NPD4730	Approved
0.6944	Remote Similarity	NPD4729	Approved
0.6941	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5208	Approved
0.6932	Remote Similarity	NPD4789	Approved
0.6932	Remote Similarity	NPD4244	Approved
0.6932	Remote Similarity	NPD4245	Approved
0.693	Remote Similarity	NPD7101	Approved
0.693	Remote Similarity	NPD7100	Approved
0.6923	Remote Similarity	NPD6933	Approved
0.6903	Remote Similarity	NPD6317	Approved
0.69	Remote Similarity	NPD5693	Phase 1
0.6897	Remote Similarity	NPD6370	Approved
0.6893	Remote Similarity	NPD7902	Approved
0.6891	Remote Similarity	NPD7736	Approved
0.6864	Remote Similarity	NPD7507	Approved
0.6863	Remote Similarity	NPD5654	Approved
0.686	Remote Similarity	NPD4224	Phase 2
0.6842	Remote Similarity	NPD6313	Approved
0.6842	Remote Similarity	NPD6314	Approved
0.6842	Remote Similarity	NPD6435	Approved
0.6832	Remote Similarity	NPD5133	Approved
0.6818	Remote Similarity	NPD5251	Approved
0.6818	Remote Similarity	NPD5248	Approved
0.6818	Remote Similarity	NPD3698	Phase 2
0.6818	Remote Similarity	NPD5247	Approved
0.6818	Remote Similarity	NPD5135	Approved
0.6818	Remote Similarity	NPD5249	Phase 3
0.6818	Remote Similarity	NPD5250	Approved
0.6818	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5169	Approved
0.6818	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6908	Approved
0.681	Remote Similarity	NPD6015	Approved
0.681	Remote Similarity	NPD6016	Approved
0.681	Remote Similarity	NPD6909	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