NPASS Compound

Structure

CID294480 OpenBabel06191716102D 36 38 0 0 1 0 0 0 0 0999 V2000 1.5180 5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0981 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 -4.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.3660 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 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1871 5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5981 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 2.5388 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 2.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 3.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9074 1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5981 1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 4 20 1 0 0 0 0 6 30 1 0 0 0 0 8 36 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 19 2 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 24 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 25 1 0 0 0 0 18 31 1 0 0 0 0 20 22 1 0 0 0 0 21 11 1 1 0 0 0 21 27 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 1 0 0 0 23 24 2 0 0 0 0 23 29 1 0 0 0 0 24 31 1 0 0 0 0 25 27 1 0 0 0 0 25 32 1 6 0 0 0 26 33 2 0 0 0 0 26 36 1 0 0 0 0 27 30 1 1 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 29 5 1 1 0 0 0 30 31 1 1 0 0 0 31 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.35
Volume:	549.831
LogP:	5.733
LogD:	3.998
LogS:	-4.986
# Rotatable Bonds:	10
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.267
Synthetic Accessibility Score:	5.015
Fsp3:	0.742
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.252
MDCK Permeability:	1.1895303941855673e-05
Pgp-inhibitor:	0.8
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.407
30% Bioavailability (F30%):	0.069

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	93.90723419189453%
Volume Distribution (VD):	0.719
Pgp-substrate:	3.808122158050537%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.459
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.319
CYP3A4-substrate:	0.284

ADMET: Excretion

Clearance (CL):	5.848
Half-life (T1/2):	0.334

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.56
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.153
Maximum Recommended Daily Dose:	0.239
Skin Sensitization:	0.177
Carcinogencity:	0.215
Eye Corrosion:	0.007
Eye Irritation:	0.021
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC294480

Natural Product ID:	NPC294480
*Common Name:**	Poricoic Acid Gm
IUPAC Name:	(2R)-2-[(2R,3R,3aR,6S,7S,9bR)-2-hydroxy-6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,4,5,7,8,9-octahydrocyclopenta[a]naphthalen-3-yl]-6-methylhept-5-enoic acid
Synonyms:	poricoic acid GM
Standard InCHIKey:	UGVHLNKATMYQSO-SMFZDKLCSA-N
Standard InCHI:	InChI=1S/C31H48O5/c1-19(2)10-9-11-21(28(34)35)27-25(32)18-31(7)24-13-12-22(20(3)4)29(5,16-15-26(33)36-8)23(24)14-17-30(27,31)6/h10,21-22,25,27,32H,3,9,11-18H2,1-2,4-8H3,(H,34,35)/t21-,22+,25-,27+,29+,30-,31+/m1/s1
SMILES:	COC(=O)CC[C@@]1(C)[C@@H](CCC2=C1CC[C@]1([C@@]2(C)C[C@H]([C@@H]1[C@H](C(=O)O)CCC=C(C)C)O)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079200
PubChem CID:	46882800
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
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	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	5

Activity Type	# Activity
Cell Line	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Inhibition	=	70.0	%	PMID[490542]
NPT2	Others	Unspecified		IC50	=	216.0	molar ratio	PMID[490542]
NPT2	Others	Unspecified		Inhibition	=	86.4	%	PMID[490542]
NPT2	Others	Unspecified		Inhibition	=	60.1	%	PMID[490542]
NPT2	Others	Unspecified		Inhibition	=	19.9	%	PMID[490542]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[490542]

☑ 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 NPC294480 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	167
0.1-0.2	1098
0.2-0.3	5534
0.3-0.4	15469
0.4-0.5	7253
0.5-0.6	6724
0.6-0.7	5246
0.7-0.8	1090
0.8-0.85	78
0.85-0.9	26
0.9-0.95	4
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC312215
0.9759	High Similarity	NPC183546
0.9756	High Similarity	NPC212843
0.9529	High Similarity	NPC123854
0.9529	High Similarity	NPC46281
0.9524	High Similarity	NPC247406
0.9524	High Similarity	NPC48866
0.9419	High Similarity	NPC154101
0.9412	High Similarity	NPC155479
0.9412	High Similarity	NPC54689
0.931	High Similarity	NPC152897
0.931	High Similarity	NPC66429
0.9205	High Similarity	NPC7165
0.9195	High Similarity	NPC23434
0.9195	High Similarity	NPC45269
0.9101	High Similarity	NPC162001
0.9101	High Similarity	NPC20546
0.9101	High Similarity	NPC184848
0.9101	High Similarity	NPC45324
0.9101	High Similarity	NPC69548
0.9101	High Similarity	NPC263347
0.9101	High Similarity	NPC222845
0.9091	High Similarity	NPC470376
0.9091	High Similarity	NPC243866
0.9091	High Similarity	NPC470375
0.9011	High Similarity	NPC477813
0.9	High Similarity	NPC155676
0.8953	High Similarity	NPC167877
0.8901	High Similarity	NPC469432
0.8901	High Similarity	NPC107243
0.8901	High Similarity	NPC57416
0.8889	High Similarity	NPC469599
0.8824	High Similarity	NPC165064
0.8804	High Similarity	NPC186810
0.8804	High Similarity	NPC48647
0.8764	High Similarity	NPC297265
0.8764	High Similarity	NPC150383
0.875	High Similarity	NPC215029
0.875	High Similarity	NPC476733
0.8736	High Similarity	NPC187376
0.8736	High Similarity	NPC233836
0.8736	High Similarity	NPC159046
0.8721	High Similarity	NPC474218
0.871	High Similarity	NPC218383
0.8696	High Similarity	NPC475894
0.8667	High Similarity	NPC206810
0.8652	High Similarity	NPC148414
0.8652	High Similarity	NPC477149
0.8652	High Similarity	NPC175628
0.8652	High Similarity	NPC111585
0.8652	High Similarity	NPC477147
0.8636	High Similarity	NPC242864
0.8632	High Similarity	NPC236390
0.8621	High Similarity	NPC28252
0.8621	High Similarity	NPC155011
0.8621	High Similarity	NPC55309
0.8617	High Similarity	NPC474327
0.8605	High Similarity	NPC82902
0.8605	High Similarity	NPC100391
0.8588	High Similarity	NPC296367
0.8588	High Similarity	NPC133391
0.8587	High Similarity	NPC173272
0.8556	High Similarity	NPC26888
0.8539	High Similarity	NPC84271
0.8539	High Similarity	NPC474704
0.8539	High Similarity	NPC477943
0.8539	High Similarity	NPC77168
0.8539	High Similarity	NPC474889
0.8539	High Similarity	NPC214387
0.8539	High Similarity	NPC102414
0.8539	High Similarity	NPC475921
0.8526	High Similarity	NPC204450
0.8526	High Similarity	NPC195290
0.8523	High Similarity	NPC474684
0.8523	High Similarity	NPC317590
0.8523	High Similarity	NPC142361
0.8523	High Similarity	NPC96496
0.8478	Intermediate Similarity	NPC48330
0.8471	Intermediate Similarity	NPC38350
0.8471	Intermediate Similarity	NPC201912
0.8462	Intermediate Similarity	NPC470224
0.8462	Intermediate Similarity	NPC25750
0.8462	Intermediate Similarity	NPC107674
0.8462	Intermediate Similarity	NPC141497
0.8462	Intermediate Similarity	NPC170220
0.8452	Intermediate Similarity	NPC477371
0.8452	Intermediate Similarity	NPC196827
0.8452	Intermediate Similarity	NPC274996
0.8444	Intermediate Similarity	NPC44240
0.8444	Intermediate Similarity	NPC471896
0.8444	Intermediate Similarity	NPC469400
0.8444	Intermediate Similarity	NPC171441
0.8438	Intermediate Similarity	NPC140723
0.8427	Intermediate Similarity	NPC28227
0.8409	Intermediate Similarity	NPC469994
0.8404	Intermediate Similarity	NPC235464
0.8404	Intermediate Similarity	NPC166745
0.8404	Intermediate Similarity	NPC197386
0.8391	Intermediate Similarity	NPC473246
0.8387	Intermediate Similarity	NPC125622
0.8387	Intermediate Similarity	NPC42042
0.8372	Intermediate Similarity	NPC260956
0.8372	Intermediate Similarity	NPC240302
0.837	Intermediate Similarity	NPC469406
0.8352	Intermediate Similarity	NPC189520
0.8352	Intermediate Similarity	NPC212301
0.8352	Intermediate Similarity	NPC86266
0.8352	Intermediate Similarity	NPC110657
0.8351	Intermediate Similarity	NPC472227
0.8351	Intermediate Similarity	NPC472228
0.8351	Intermediate Similarity	NPC477812
0.8333	Intermediate Similarity	NPC321514
0.8333	Intermediate Similarity	NPC474570
0.8333	Intermediate Similarity	NPC474679
0.8333	Intermediate Similarity	NPC473928
0.8316	Intermediate Similarity	NPC205899
0.8316	Intermediate Similarity	NPC476274
0.8315	Intermediate Similarity	NPC134197
0.8298	Intermediate Similarity	NPC18319
0.8295	Intermediate Similarity	NPC329738
0.8295	Intermediate Similarity	NPC474083
0.8295	Intermediate Similarity	NPC283733
0.828	Intermediate Similarity	NPC241156
0.828	Intermediate Similarity	NPC470016
0.828	Intermediate Similarity	NPC317586
0.8276	Intermediate Similarity	NPC83569
0.8276	Intermediate Similarity	NPC477373
0.8276	Intermediate Similarity	NPC69279
0.8276	Intermediate Similarity	NPC310470
0.8276	Intermediate Similarity	NPC245866
0.8261	Intermediate Similarity	NPC470254
0.8261	Intermediate Similarity	NPC109414
0.8261	Intermediate Similarity	NPC472942
0.8256	Intermediate Similarity	NPC147066
0.8256	Intermediate Similarity	NPC477372
0.8256	Intermediate Similarity	NPC327002
0.8242	Intermediate Similarity	NPC320026
0.8242	Intermediate Similarity	NPC69622
0.8235	Intermediate Similarity	NPC327674
0.8229	Intermediate Similarity	NPC99411
0.8229	Intermediate Similarity	NPC476223
0.8229	Intermediate Similarity	NPC476240
0.8229	Intermediate Similarity	NPC224720
0.8222	Intermediate Similarity	NPC328313
0.8222	Intermediate Similarity	NPC470417
0.8211	Intermediate Similarity	NPC10364
0.8211	Intermediate Similarity	NPC477854
0.8202	Intermediate Similarity	NPC73038
0.8202	Intermediate Similarity	NPC195640
0.8202	Intermediate Similarity	NPC80590
0.8202	Intermediate Similarity	NPC94755
0.8202	Intermediate Similarity	NPC6979
0.8191	Intermediate Similarity	NPC472941
0.8191	Intermediate Similarity	NPC322063
0.8191	Intermediate Similarity	NPC95565
0.8191	Intermediate Similarity	NPC328371
0.8191	Intermediate Similarity	NPC456
0.8191	Intermediate Similarity	NPC120708
0.8182	Intermediate Similarity	NPC214043
0.8182	Intermediate Similarity	NPC221758
0.8182	Intermediate Similarity	NPC321187
0.8182	Intermediate Similarity	NPC194937
0.8182	Intermediate Similarity	NPC476038
0.8182	Intermediate Similarity	NPC85774
0.8182	Intermediate Similarity	NPC58841
0.8182	Intermediate Similarity	NPC263974
0.8182	Intermediate Similarity	NPC59453
0.8182	Intermediate Similarity	NPC329043
0.8182	Intermediate Similarity	NPC161423
0.8182	Intermediate Similarity	NPC227064
0.8172	Intermediate Similarity	NPC166906
0.8172	Intermediate Similarity	NPC49670
0.8172	Intermediate Similarity	NPC111015
0.8172	Intermediate Similarity	NPC159410
0.8163	Intermediate Similarity	NPC235889
0.8152	Intermediate Similarity	NPC107690
0.8144	Intermediate Similarity	NPC56498
0.8144	Intermediate Similarity	NPC22388
0.8132	Intermediate Similarity	NPC128496
0.8132	Intermediate Similarity	NPC76879
0.8132	Intermediate Similarity	NPC2983
0.8132	Intermediate Similarity	NPC310236
0.8125	Intermediate Similarity	NPC167974
0.8125	Intermediate Similarity	NPC51370
0.8125	Intermediate Similarity	NPC241221
0.8125	Intermediate Similarity	NPC287833
0.8111	Intermediate Similarity	NPC136548
0.8111	Intermediate Similarity	NPC477926
0.8111	Intermediate Similarity	NPC90652
0.8111	Intermediate Similarity	NPC128644
0.809	Intermediate Similarity	NPC323765
0.809	Intermediate Similarity	NPC470223
0.809	Intermediate Similarity	NPC471224
0.8085	Intermediate Similarity	NPC173875
0.8085	Intermediate Similarity	NPC279974
0.8085	Intermediate Similarity	NPC174948
0.8085	Intermediate Similarity	NPC469995
0.8085	Intermediate Similarity	NPC318282
0.8085	Intermediate Similarity	NPC472932
0.8081	Intermediate Similarity	NPC278628

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 NPC294480 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1700
0.2-0.3	3974
0.3-0.4	2270
0.4-0.5	557
0.5-0.6	205
0.6-0.7	197
0.7-0.8	97
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD6399	Phase 3
0.8352	Intermediate Similarity	NPD5281	Approved
0.8352	Intermediate Similarity	NPD5284	Approved
0.8298	Intermediate Similarity	NPD6083	Phase 2
0.8298	Intermediate Similarity	NPD6084	Phase 2
0.828	Intermediate Similarity	NPD5695	Phase 3
0.8202	Intermediate Similarity	NPD7334	Approved
0.8202	Intermediate Similarity	NPD7521	Approved
0.8202	Intermediate Similarity	NPD7146	Approved
0.8202	Intermediate Similarity	NPD6409	Approved
0.8202	Intermediate Similarity	NPD5330	Approved
0.8202	Intermediate Similarity	NPD6684	Approved
0.8182	Intermediate Similarity	NPD3133	Approved
0.8182	Intermediate Similarity	NPD3666	Approved
0.8182	Intermediate Similarity	NPD3665	Phase 1
0.8182	Intermediate Similarity	NPD4786	Approved
0.8081	Intermediate Similarity	NPD7128	Approved
0.8081	Intermediate Similarity	NPD6675	Approved
0.8081	Intermediate Similarity	NPD6402	Approved
0.8081	Intermediate Similarity	NPD5739	Approved
0.8022	Intermediate Similarity	NPD6903	Approved
0.8022	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD5696	Approved
0.802	Intermediate Similarity	NPD6373	Approved
0.802	Intermediate Similarity	NPD6372	Approved
0.7955	Intermediate Similarity	NPD3667	Approved
0.7935	Intermediate Similarity	NPD4753	Phase 2
0.7921	Intermediate Similarity	NPD7320	Approved
0.7921	Intermediate Similarity	NPD6899	Approved
0.7921	Intermediate Similarity	NPD6881	Approved
0.7872	Intermediate Similarity	NPD4202	Approved
0.7865	Intermediate Similarity	NPD5362	Discontinued
0.7864	Intermediate Similarity	NPD6650	Approved
0.7864	Intermediate Similarity	NPD6649	Approved
0.7841	Intermediate Similarity	NPD5369	Approved
0.7826	Intermediate Similarity	NPD6672	Approved
0.7826	Intermediate Similarity	NPD5737	Approved
0.7822	Intermediate Similarity	NPD5697	Approved
0.7822	Intermediate Similarity	NPD5701	Approved
0.7802	Intermediate Similarity	NPD6098	Approved
0.7802	Intermediate Similarity	NPD3618	Phase 1
0.7802	Intermediate Similarity	NPD5279	Phase 3
0.7767	Intermediate Similarity	NPD7290	Approved
0.7767	Intermediate Similarity	NPD6883	Approved
0.7767	Intermediate Similarity	NPD7102	Approved
0.7766	Intermediate Similarity	NPD8034	Phase 2
0.7766	Intermediate Similarity	NPD8035	Phase 2
0.7766	Intermediate Similarity	NPD6050	Approved
0.7753	Intermediate Similarity	NPD4221	Approved
0.7753	Intermediate Similarity	NPD4223	Phase 3
0.7753	Intermediate Similarity	NPD6435	Approved
0.7745	Intermediate Similarity	NPD6011	Approved
0.7742	Intermediate Similarity	NPD6673	Approved
0.7742	Intermediate Similarity	NPD5328	Approved
0.7742	Intermediate Similarity	NPD6080	Approved
0.7742	Intermediate Similarity	NPD6904	Approved
0.7732	Intermediate Similarity	NPD4755	Approved
0.7727	Intermediate Similarity	NPD5368	Approved
0.7708	Intermediate Similarity	NPD5210	Approved
0.7708	Intermediate Similarity	NPD4629	Approved
0.7708	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6869	Approved
0.7692	Intermediate Similarity	NPD6617	Approved
0.7692	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8130	Phase 1
0.7692	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5329	Approved
0.7692	Intermediate Similarity	NPD6847	Approved
0.767	Intermediate Similarity	NPD6013	Approved
0.767	Intermediate Similarity	NPD6012	Approved
0.767	Intermediate Similarity	NPD6014	Approved
0.766	Intermediate Similarity	NPD5207	Approved
0.766	Intermediate Similarity	NPD5692	Phase 3
0.7619	Intermediate Similarity	NPD6882	Approved
0.7619	Intermediate Similarity	NPD8297	Approved
0.7609	Intermediate Similarity	NPD5690	Phase 2
0.7609	Intermediate Similarity	NPD5280	Approved
0.7609	Intermediate Similarity	NPD4694	Approved
0.7582	Intermediate Similarity	NPD4197	Approved
0.7579	Intermediate Similarity	NPD6079	Approved
0.7579	Intermediate Similarity	NPD7515	Phase 2
0.7579	Intermediate Similarity	NPD5694	Approved
0.7579	Intermediate Similarity	NPD6411	Approved
0.7576	Intermediate Similarity	NPD5286	Approved
0.7576	Intermediate Similarity	NPD4700	Approved
0.7576	Intermediate Similarity	NPD5285	Approved
0.7576	Intermediate Similarity	NPD4696	Approved
0.7556	Intermediate Similarity	NPD4270	Approved
0.7556	Intermediate Similarity	NPD4269	Approved
0.7551	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD6412	Phase 2
0.7475	Intermediate Similarity	NPD7638	Approved
0.7474	Intermediate Similarity	NPD5785	Approved
0.7473	Intermediate Similarity	NPD4788	Approved
0.7471	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD4697	Phase 3
0.7447	Intermediate Similarity	NPD5208	Approved
0.7444	Intermediate Similarity	NPD4692	Approved
0.7444	Intermediate Similarity	NPD4139	Approved
0.7426	Intermediate Similarity	NPD4633	Approved
0.7426	Intermediate Similarity	NPD5225	Approved
0.7426	Intermediate Similarity	NPD5224	Approved
0.7426	Intermediate Similarity	NPD5226	Approved
0.7426	Intermediate Similarity	NPD5211	Phase 2
0.7423	Intermediate Similarity	NPD7748	Approved
0.7419	Intermediate Similarity	NPD4138	Approved
0.7419	Intermediate Similarity	NPD5786	Approved
0.7419	Intermediate Similarity	NPD4689	Approved
0.7419	Intermediate Similarity	NPD5205	Approved
0.7419	Intermediate Similarity	NPD4690	Approved
0.7419	Intermediate Similarity	NPD4693	Phase 3
0.7419	Intermediate Similarity	NPD4688	Approved
0.74	Intermediate Similarity	NPD7640	Approved
0.74	Intermediate Similarity	NPD7639	Approved
0.7396	Intermediate Similarity	NPD5693	Phase 1
0.7391	Intermediate Similarity	NPD3668	Phase 3
0.7383	Intermediate Similarity	NPD4632	Approved
0.7379	Intermediate Similarity	NPD6008	Approved
0.7368	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6101	Approved
0.7368	Intermediate Similarity	NPD6051	Approved
0.7356	Intermediate Similarity	NPD6942	Approved
0.7356	Intermediate Similarity	NPD7339	Approved
0.7353	Intermediate Similarity	NPD4754	Approved
0.7353	Intermediate Similarity	NPD5174	Approved
0.7353	Intermediate Similarity	NPD5175	Approved
0.7333	Intermediate Similarity	NPD4820	Approved
0.7333	Intermediate Similarity	NPD7525	Registered
0.7333	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4821	Approved
0.7333	Intermediate Similarity	NPD4819	Approved
0.7333	Intermediate Similarity	NPD4822	Approved
0.7333	Intermediate Similarity	NPD4252	Approved
0.7312	Intermediate Similarity	NPD5363	Approved
0.7303	Intermediate Similarity	NPD4271	Approved
0.7303	Intermediate Similarity	NPD4268	Approved
0.729	Intermediate Similarity	NPD6053	Discontinued
0.7283	Intermediate Similarity	NPD5331	Approved
0.7283	Intermediate Similarity	NPD5332	Approved
0.7282	Intermediate Similarity	NPD5141	Approved
0.7273	Intermediate Similarity	NPD5221	Approved
0.7273	Intermediate Similarity	NPD5222	Approved
0.7273	Intermediate Similarity	NPD6335	Approved
0.7273	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4790	Discontinued
0.7248	Intermediate Similarity	NPD6274	Approved
0.7245	Intermediate Similarity	NPD7900	Approved
0.7245	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6001	Approved
0.7234	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4767	Approved
0.7212	Intermediate Similarity	NPD4768	Approved
0.7209	Intermediate Similarity	NPD4243	Approved
0.7207	Intermediate Similarity	NPD7101	Approved
0.7207	Intermediate Similarity	NPD7100	Approved
0.72	Intermediate Similarity	NPD5173	Approved
0.7191	Intermediate Similarity	NPD6116	Phase 1
0.7182	Intermediate Similarity	NPD6317	Approved
0.7182	Intermediate Similarity	NPD6009	Approved
0.7172	Intermediate Similarity	NPD5654	Approved
0.7143	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD5779	Approved
0.7117	Intermediate Similarity	NPD6314	Approved
0.7117	Intermediate Similarity	NPD6313	Approved
0.7113	Intermediate Similarity	NPD4096	Approved
0.7097	Intermediate Similarity	NPD7154	Phase 3
0.7083	Intermediate Similarity	NPD4518	Approved
0.708	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6909	Approved
0.708	Intermediate Similarity	NPD6908	Approved
0.7079	Intermediate Similarity	NPD6117	Approved
0.7075	Intermediate Similarity	NPD5128	Approved
0.7075	Intermediate Similarity	NPD4729	Approved
0.7075	Intermediate Similarity	NPD4730	Approved
0.7045	Intermediate Similarity	NPD6924	Approved
0.7045	Intermediate Similarity	NPD4785	Approved
0.7045	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4784	Approved
0.7045	Intermediate Similarity	NPD6926	Approved
0.7041	Intermediate Similarity	NPD7637	Suspended
0.7033	Intermediate Similarity	NPD4195	Approved
0.703	Intermediate Similarity	NPD5959	Approved
0.7027	Intermediate Similarity	NPD7115	Discovery
0.7019	Intermediate Similarity	NPD6052	Approved
0.701	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6319	Approved
0.6989	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5133	Approved
0.6966	Remote Similarity	NPD3702	Approved
0.6957	Remote Similarity	NPD4748	Discontinued
0.6957	Remote Similarity	NPD7604	Phase 2
0.6944	Remote Similarity	NPD5169	Approved
0.6944	Remote Similarity	NPD5250	Approved
0.6944	Remote Similarity	NPD5247	Approved
0.6944	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5249	Phase 3
0.6944	Remote Similarity	NPD5135	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