NPASS Compound

Structure

NPC243866 OpenBabel07101718332D 36 39 0 0 1 0 0 0 0 0999 V2000 0.5398 5.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4905 3.8204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5394 3.5114 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 -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 0.9000 3.9543 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 -0.8660 -1.5000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -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 0.2308 4.6974 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 -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 -2.5981 -1.5000 0.0000 C 0 0 1 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 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7473 4.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 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 -5.1962 -2.0000 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 -1.4164 5.2327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 22 1 0 0 0 0 17 31 1 0 0 0 0 18 28 1 0 0 0 0 19 10 1 1 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 20 21 2 0 0 0 0 20 29 1 0 0 0 0 21 31 1 0 0 0 0 22 25 1 0 0 0 0 22 32 1 6 0 0 0 23 27 1 0 0 0 0 23 29 1 1 0 0 0 24 27 1 0 0 0 0 24 33 2 0 0 0 0 25 30 1 1 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 28 36 1 0 0 0 0 29 6 1 1 0 0 0 30 31 1 1 0 0 0 31 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.35
Volume:	543.911
LogP:	3.759
LogD:	2.82
LogS:	-4.148
# 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:	0.384
Synthetic Accessibility Score:	5.099
Fsp3:	0.806
Lipinski Rule-of-5:	Accepted
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:	-5.382
MDCK Permeability:	1.0485033271834254e-05
Pgp-inhibitor:	0.161
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.327
30% Bioavailability (F30%):	0.435

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	81.45729064941406%
Volume Distribution (VD):	0.644
Pgp-substrate:	5.4335551261901855%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.643
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.941
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.3
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	3.906
Half-life (T1/2):	0.773

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.313
Drug-inuced Liver Injury (DILI):	0.059
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.4
Skin Sensitization:	0.022
Carcinogencity:	0.072
Eye Corrosion:	0.004
Eye Irritation:	0.03
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC243866

Natural Product ID:	NPC243866
*Common Name:**	(20Zeta)-3-Oxo-16Alpha,25-Dihydroxy-24-Methyllanosta-8,24(241)-Dien-21-Oic Acid
IUPAC Name:	(2R)-6-hydroxy-2-[(5R,10S,13R,14R,16R,17R)-16-hydroxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms:	16alpha,25-Dihydroxyeburiconic Acid
Standard InCHIKey:	YEXYFLGTSGQWMI-IMOFTLGFSA-N
Standard InCHI:	InChI=1S/C31H48O5/c1-18(28(4,5)36)9-10-19(26(34)35)25-22(32)17-31(8)21-11-12-23-27(2,3)24(33)14-15-29(23,6)20(21)13-16-30(25,31)7/h19,22-23,25,32,36H,1,9-17H2,2-8H3,(H,34,35)/t19-,22-,23+,25+,29-,30-,31+/m1/s1
SMILES:	C=C(CC[C@H]([C@H]1[C@@H](C[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1CC3)O)C(=O)O)C(C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077753
PubChem CID:	46882674
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	3
Others	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	84700.0	nM	PMID[458344]
NPT80	Cell Line	Raji	Homo sapiens	Inhibition	=	70.0	%	PMID[458344]
NPT2	Others	Unspecified		IC50	=	299.0	molar ratio	PMID[458344]
NPT2	Others	Unspecified		Inhibition	=	96.1	%	PMID[458344]
NPT2	Others	Unspecified		Inhibition	=	72.2	%	PMID[458344]
NPT2	Others	Unspecified		Inhibition	=	36.1	%	PMID[458344]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[458344]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	28700.0	nM	PMID[458344]

☑ 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 NPC243866 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	162
0.1-0.2	1155
0.2-0.3	5319
0.3-0.4	14603
0.4-0.5	7548
0.5-0.6	6150
0.6-0.7	5812
0.7-0.8	1634
0.8-0.85	212
0.85-0.9	85
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9663	High Similarity	NPC155676
0.9651	High Similarity	NPC54689
0.9651	High Similarity	NPC155479
0.9341	High Similarity	NPC107243
0.9326	High Similarity	NPC152897
0.9326	High Similarity	NPC66429
0.9302	High Similarity	NPC212843
0.9239	High Similarity	NPC186810
0.9213	High Similarity	NPC154101
0.9213	High Similarity	NPC23434
0.9213	High Similarity	NPC45269
0.9195	High Similarity	NPC312215
0.913	High Similarity	NPC57416
0.9121	High Similarity	NPC263347
0.9101	High Similarity	NPC469400
0.9091	High Similarity	NPC183546
0.9091	High Similarity	NPC294480
0.9032	High Similarity	NPC48647
0.9011	High Similarity	NPC7165
0.9	High Similarity	NPC150383
0.8947	High Similarity	NPC195290
0.8947	High Similarity	NPC204450
0.8936	High Similarity	NPC218383
0.8925	High Similarity	NPC475894
0.8913	High Similarity	NPC222845
0.8913	High Similarity	NPC69548
0.8913	High Similarity	NPC45324
0.8913	High Similarity	NPC184848
0.8913	High Similarity	NPC162001
0.8901	High Similarity	NPC470376
0.8901	High Similarity	NPC206810
0.8901	High Similarity	NPC470375
0.8889	High Similarity	NPC46281
0.8876	High Similarity	NPC48866
0.8876	High Similarity	NPC247406
0.8864	High Similarity	NPC469994
0.8854	High Similarity	NPC236390
0.8851	High Similarity	NPC165064
0.883	High Similarity	NPC197386
0.883	High Similarity	NPC235464
0.883	High Similarity	NPC10364
0.883	High Similarity	NPC166745
0.8791	High Similarity	NPC107690
0.8778	High Similarity	NPC2983
0.8778	High Similarity	NPC214387
0.8764	High Similarity	NPC317590
0.875	High Similarity	NPC474218
0.875	High Similarity	NPC474083
0.8737	High Similarity	NPC205899
0.8723	High Similarity	NPC469432
0.8723	High Similarity	NPC18319
0.871	High Similarity	NPC174948
0.871	High Similarity	NPC469599
0.871	High Similarity	NPC469995
0.871	High Similarity	NPC318282
0.871	High Similarity	NPC173875
0.871	High Similarity	NPC20546
0.8696	High Similarity	NPC472942
0.8696	High Similarity	NPC470254
0.8696	High Similarity	NPC25750
0.8681	High Similarity	NPC320026
0.8681	High Similarity	NPC477147
0.8681	High Similarity	NPC123854
0.8681	High Similarity	NPC171441
0.8681	High Similarity	NPC69622
0.8681	High Similarity	NPC477149
0.8667	High Similarity	NPC242864
0.8652	High Similarity	NPC28252
0.8652	High Similarity	NPC55309
0.8646	High Similarity	NPC163372
0.8646	High Similarity	NPC474327
0.8646	High Similarity	NPC302537
0.8636	High Similarity	NPC82902
0.8632	High Similarity	NPC477813
0.8617	High Similarity	NPC472941
0.8617	High Similarity	NPC456
0.8617	High Similarity	NPC328371
0.8602	High Similarity	NPC469406
0.8587	High Similarity	NPC297265
0.8571	High Similarity	NPC476733
0.8571	High Similarity	NPC477943
0.8571	High Similarity	NPC215029
0.8557	High Similarity	NPC308726
0.8557	High Similarity	NPC56498
0.8557	High Similarity	NPC119601
0.8556	High Similarity	NPC136948
0.8556	High Similarity	NPC187376
0.8556	High Similarity	NPC96496
0.8556	High Similarity	NPC159046
0.8556	High Similarity	NPC233836
0.8542	High Similarity	NPC287833
0.8542	High Similarity	NPC51370
0.8542	High Similarity	NPC154072
0.8539	High Similarity	NPC471224
0.8526	High Similarity	NPC320306
0.8511	High Similarity	NPC48330
0.8511	High Similarity	NPC472932
0.8511	High Similarity	NPC37646
0.8511	High Similarity	NPC241156
0.8506	High Similarity	NPC38350
0.8506	High Similarity	NPC201912
0.8478	Intermediate Similarity	NPC289213
0.8469	Intermediate Similarity	NPC55872
0.8462	Intermediate Similarity	NPC470417
0.8454	Intermediate Similarity	NPC99411
0.8444	Intermediate Similarity	NPC155011
0.8444	Intermediate Similarity	NPC322159
0.8444	Intermediate Similarity	NPC70661
0.8427	Intermediate Similarity	NPC473246
0.8427	Intermediate Similarity	NPC263974
0.8421	Intermediate Similarity	NPC125622
0.8421	Intermediate Similarity	NPC3772
0.8421	Intermediate Similarity	NPC95565
0.8421	Intermediate Similarity	NPC235053
0.8421	Intermediate Similarity	NPC40765
0.8421	Intermediate Similarity	NPC322063
0.8421	Intermediate Similarity	NPC243525
0.8421	Intermediate Similarity	NPC173272
0.8421	Intermediate Similarity	NPC42042
0.8409	Intermediate Similarity	NPC133391
0.8409	Intermediate Similarity	NPC260956
0.8409	Intermediate Similarity	NPC170985
0.8409	Intermediate Similarity	NPC145143
0.8404	Intermediate Similarity	NPC184870
0.8404	Intermediate Similarity	NPC166906
0.8387	Intermediate Similarity	NPC204341
0.8387	Intermediate Similarity	NPC86266
0.8387	Intermediate Similarity	NPC212301
0.8387	Intermediate Similarity	NPC110657
0.8384	Intermediate Similarity	NPC28656
0.837	Intermediate Similarity	NPC84271
0.837	Intermediate Similarity	NPC262043
0.837	Intermediate Similarity	NPC102414
0.837	Intermediate Similarity	NPC474704
0.837	Intermediate Similarity	NPC474889
0.837	Intermediate Similarity	NPC475921
0.837	Intermediate Similarity	NPC77168
0.837	Intermediate Similarity	NPC76879
0.8367	Intermediate Similarity	NPC473928
0.8367	Intermediate Similarity	NPC234892
0.8367	Intermediate Similarity	NPC293753
0.8352	Intermediate Similarity	NPC142361
0.8352	Intermediate Similarity	NPC167877
0.8352	Intermediate Similarity	NPC474684
0.8352	Intermediate Similarity	NPC90652
0.8351	Intermediate Similarity	NPC316964
0.8351	Intermediate Similarity	NPC327431
0.8351	Intermediate Similarity	NPC476274
0.8333	Intermediate Similarity	NPC106557
0.8333	Intermediate Similarity	NPC121339
0.8333	Intermediate Similarity	NPC122294
0.8316	Intermediate Similarity	NPC317586
0.8316	Intermediate Similarity	NPC470016
0.8316	Intermediate Similarity	NPC476174
0.8315	Intermediate Similarity	NPC83569
0.8315	Intermediate Similarity	NPC477373
0.8315	Intermediate Similarity	NPC310470
0.8315	Intermediate Similarity	NPC168188
0.8315	Intermediate Similarity	NPC470015
0.8315	Intermediate Similarity	NPC69279
0.8315	Intermediate Similarity	NPC245866
0.83	Intermediate Similarity	NPC323834
0.8298	Intermediate Similarity	NPC107674
0.8298	Intermediate Similarity	NPC170220
0.8298	Intermediate Similarity	NPC472930
0.8298	Intermediate Similarity	NPC141497
0.8295	Intermediate Similarity	NPC147066
0.8283	Intermediate Similarity	NPC140723
0.8283	Intermediate Similarity	NPC111323
0.828	Intermediate Similarity	NPC111585
0.828	Intermediate Similarity	NPC44240
0.828	Intermediate Similarity	NPC148414
0.828	Intermediate Similarity	NPC175628
0.8276	Intermediate Similarity	NPC477371
0.8265	Intermediate Similarity	NPC472924
0.8265	Intermediate Similarity	NPC476223
0.8265	Intermediate Similarity	NPC476240
0.8265	Intermediate Similarity	NPC224720
0.8261	Intermediate Similarity	NPC44181
0.8261	Intermediate Similarity	NPC328313
0.8261	Intermediate Similarity	NPC28227
0.8247	Intermediate Similarity	NPC471717
0.8247	Intermediate Similarity	NPC16021
0.8242	Intermediate Similarity	NPC80590
0.8242	Intermediate Similarity	NPC475007
0.8242	Intermediate Similarity	NPC472494
0.8242	Intermediate Similarity	NPC89077
0.8242	Intermediate Similarity	NPC472491
0.8242	Intermediate Similarity	NPC72133
0.8229	Intermediate Similarity	NPC249954
0.8229	Intermediate Similarity	NPC328162
0.8229	Intermediate Similarity	NPC7124
0.8229	Intermediate Similarity	NPC96859
0.8229	Intermediate Similarity	NPC305483
0.8229	Intermediate Similarity	NPC49371
0.8222	Intermediate Similarity	NPC476038
0.8222	Intermediate Similarity	NPC58841
0.8222	Intermediate Similarity	NPC321187
0.8222	Intermediate Similarity	NPC161423
0.8222	Intermediate Similarity	NPC227064

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 NPC243866 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1568
0.2-0.3	4021
0.3-0.4	2339
0.4-0.5	576
0.5-0.6	179
0.6-0.7	161
0.7-0.8	150
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8587	High Similarity	NPD5284	Approved
0.8587	High Similarity	NPD5281	Approved
0.8495	Intermediate Similarity	NPD6399	Phase 3
0.8333	Intermediate Similarity	NPD6084	Phase 2
0.8333	Intermediate Similarity	NPD6083	Phase 2
0.8316	Intermediate Similarity	NPD5695	Phase 3
0.8222	Intermediate Similarity	NPD3665	Phase 1
0.8222	Intermediate Similarity	NPD3133	Approved
0.8222	Intermediate Similarity	NPD3666	Approved
0.8222	Intermediate Similarity	NPD4786	Approved
0.8172	Intermediate Similarity	NPD4753	Phase 2
0.8119	Intermediate Similarity	NPD6675	Approved
0.8119	Intermediate Similarity	NPD6402	Approved
0.8119	Intermediate Similarity	NPD5739	Approved
0.8119	Intermediate Similarity	NPD7128	Approved
0.8105	Intermediate Similarity	NPD4202	Approved
0.8061	Intermediate Similarity	NPD5696	Approved
0.8058	Intermediate Similarity	NPD6372	Approved
0.8058	Intermediate Similarity	NPD6373	Approved
0.8043	Intermediate Similarity	NPD5330	Approved
0.8043	Intermediate Similarity	NPD7334	Approved
0.8043	Intermediate Similarity	NPD6684	Approved
0.8043	Intermediate Similarity	NPD7146	Approved
0.8043	Intermediate Similarity	NPD7521	Approved
0.8043	Intermediate Similarity	NPD6409	Approved
0.8	Intermediate Similarity	NPD3667	Approved
0.8	Intermediate Similarity	NPD5211	Phase 2
0.8	Intermediate Similarity	NPD4221	Approved
0.8	Intermediate Similarity	NPD4223	Phase 3
0.7961	Intermediate Similarity	NPD7320	Approved
0.7961	Intermediate Similarity	NPD6899	Approved
0.7961	Intermediate Similarity	NPD6881	Approved
0.7959	Intermediate Similarity	NPD4755	Approved
0.7938	Intermediate Similarity	NPD5210	Approved
0.7938	Intermediate Similarity	NPD4629	Approved
0.7935	Intermediate Similarity	NPD5329	Approved
0.7912	Intermediate Similarity	NPD4788	Approved
0.7905	Intermediate Similarity	NPD6649	Approved
0.7905	Intermediate Similarity	NPD6650	Approved
0.7889	Intermediate Similarity	NPD4139	Approved
0.7889	Intermediate Similarity	NPD4692	Approved
0.7872	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD6903	Approved
0.7864	Intermediate Similarity	NPD5701	Approved
0.7864	Intermediate Similarity	NPD5697	Approved
0.7849	Intermediate Similarity	NPD5280	Approved
0.7849	Intermediate Similarity	NPD4694	Approved
0.7849	Intermediate Similarity	NPD5279	Phase 3
0.7849	Intermediate Similarity	NPD6098	Approved
0.7849	Intermediate Similarity	NPD5690	Phase 2
0.7849	Intermediate Similarity	NPD3618	Phase 1
0.7843	Intermediate Similarity	NPD5141	Approved
0.7826	Intermediate Similarity	NPD4197	Approved
0.7812	Intermediate Similarity	NPD6050	Approved
0.781	Intermediate Similarity	NPD7102	Approved
0.781	Intermediate Similarity	NPD6883	Approved
0.781	Intermediate Similarity	NPD7290	Approved
0.78	Intermediate Similarity	NPD5286	Approved
0.78	Intermediate Similarity	NPD4700	Approved
0.78	Intermediate Similarity	NPD4696	Approved
0.78	Intermediate Similarity	NPD5285	Approved
0.7789	Intermediate Similarity	NPD6904	Approved
0.7789	Intermediate Similarity	NPD6080	Approved
0.7789	Intermediate Similarity	NPD6673	Approved
0.7789	Intermediate Similarity	NPD5328	Approved
0.7788	Intermediate Similarity	NPD6011	Approved
0.7755	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6847	Approved
0.7736	Intermediate Similarity	NPD8130	Phase 1
0.7736	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6617	Approved
0.7736	Intermediate Similarity	NPD6869	Approved
0.7723	Intermediate Similarity	NPD5223	Approved
0.7714	Intermediate Similarity	NPD6012	Approved
0.7714	Intermediate Similarity	NPD6014	Approved
0.7714	Intermediate Similarity	NPD6013	Approved
0.7708	Intermediate Similarity	NPD5692	Phase 3
0.7708	Intermediate Similarity	NPD5207	Approved
0.7684	Intermediate Similarity	NPD6672	Approved
0.7684	Intermediate Similarity	NPD5737	Approved
0.7664	Intermediate Similarity	NPD8297	Approved
0.7664	Intermediate Similarity	NPD6882	Approved
0.766	Intermediate Similarity	NPD4689	Approved
0.766	Intermediate Similarity	NPD4690	Approved
0.766	Intermediate Similarity	NPD4693	Phase 3
0.766	Intermediate Similarity	NPD4688	Approved
0.766	Intermediate Similarity	NPD5205	Approved
0.766	Intermediate Similarity	NPD4138	Approved
0.7647	Intermediate Similarity	NPD4633	Approved
0.7647	Intermediate Similarity	NPD5226	Approved
0.7647	Intermediate Similarity	NPD5224	Approved
0.7647	Intermediate Similarity	NPD5225	Approved
0.7629	Intermediate Similarity	NPD6079	Approved
0.7629	Intermediate Similarity	NPD7515	Phase 2
0.7629	Intermediate Similarity	NPD5693	Phase 1
0.7629	Intermediate Similarity	NPD8035	Phase 2
0.7629	Intermediate Similarity	NPD5694	Approved
0.7629	Intermediate Similarity	NPD8034	Phase 2
0.7609	Intermediate Similarity	NPD4269	Approved
0.7609	Intermediate Similarity	NPD4270	Approved
0.7573	Intermediate Similarity	NPD5174	Approved
0.7573	Intermediate Similarity	NPD5175	Approved
0.7573	Intermediate Similarity	NPD4754	Approved
0.7527	Intermediate Similarity	NPD5362	Discontinued
0.75	Intermediate Similarity	NPD5208	Approved
0.75	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD5369	Approved
0.7474	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7639	Approved
0.7451	Intermediate Similarity	NPD7640	Approved
0.7447	Intermediate Similarity	NPD3668	Phase 3
0.7431	Intermediate Similarity	NPD4632	Approved
0.7429	Intermediate Similarity	NPD4768	Approved
0.7429	Intermediate Similarity	NPD4767	Approved
0.7429	Intermediate Similarity	NPD6008	Approved
0.7426	Intermediate Similarity	NPD7902	Approved
0.7423	Intermediate Similarity	NPD6051	Approved
0.7391	Intermediate Similarity	NPD4252	Approved
0.7391	Intermediate Similarity	NPD4820	Approved
0.7391	Intermediate Similarity	NPD4822	Approved
0.7391	Intermediate Similarity	NPD4819	Approved
0.7391	Intermediate Similarity	NPD5368	Approved
0.7391	Intermediate Similarity	NPD7525	Registered
0.7391	Intermediate Similarity	NPD4821	Approved
0.7387	Intermediate Similarity	NPD7115	Discovery
0.7368	Intermediate Similarity	NPD5363	Approved
0.7358	Intermediate Similarity	NPD6412	Phase 2
0.7353	Intermediate Similarity	NPD7638	Approved
0.7347	Intermediate Similarity	NPD4096	Approved
0.7347	Intermediate Similarity	NPD5785	Approved
0.7333	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD5222	Approved
0.7327	Intermediate Similarity	NPD5221	Approved
0.7327	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6335	Approved
0.73	Intermediate Similarity	NPD7748	Approved
0.73	Intermediate Similarity	NPD6001	Approved
0.7297	Intermediate Similarity	NPD6274	Approved
0.7292	Intermediate Similarity	NPD5786	Approved
0.729	Intermediate Similarity	NPD4729	Approved
0.729	Intermediate Similarity	NPD4730	Approved
0.729	Intermediate Similarity	NPD5128	Approved
0.7283	Intermediate Similarity	NPD4195	Approved
0.7273	Intermediate Similarity	NPD4243	Approved
0.7257	Intermediate Similarity	NPD7100	Approved
0.7257	Intermediate Similarity	NPD7101	Approved
0.7255	Intermediate Similarity	NPD5173	Approved
0.7253	Intermediate Similarity	NPD6116	Phase 1
0.7234	Intermediate Similarity	NPD6435	Approved
0.7232	Intermediate Similarity	NPD6317	Approved
0.7232	Intermediate Similarity	NPD6009	Approved
0.7228	Intermediate Similarity	NPD5654	Approved
0.7222	Intermediate Similarity	NPD6942	Approved
0.7222	Intermediate Similarity	NPD7339	Approved
0.7216	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4748	Discontinued
0.72	Intermediate Similarity	NPD5133	Approved
0.7182	Intermediate Similarity	NPD6053	Discontinued
0.7174	Intermediate Similarity	NPD4271	Approved
0.7174	Intermediate Similarity	NPD4268	Approved
0.7174	Intermediate Similarity	NPD3617	Approved
0.7168	Intermediate Similarity	NPD6313	Approved
0.7168	Intermediate Similarity	NPD6314	Approved
0.7159	Intermediate Similarity	NPD4245	Approved
0.7159	Intermediate Similarity	NPD4244	Approved
0.7158	Intermediate Similarity	NPD5331	Approved
0.7158	Intermediate Similarity	NPD5332	Approved
0.7156	Intermediate Similarity	NPD5135	Approved
0.7156	Intermediate Similarity	NPD5249	Phase 3
0.7156	Intermediate Similarity	NPD5169	Approved
0.7156	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5251	Approved
0.7156	Intermediate Similarity	NPD5250	Approved
0.7156	Intermediate Similarity	NPD4634	Approved
0.7156	Intermediate Similarity	NPD5248	Approved
0.7156	Intermediate Similarity	NPD5247	Approved
0.7143	Intermediate Similarity	NPD4518	Approved
0.7143	Intermediate Similarity	NPD6117	Approved
0.713	Intermediate Similarity	NPD6908	Approved
0.713	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6909	Approved
0.7129	Intermediate Similarity	NPD7900	Approved
0.7129	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4790	Discontinued
0.7115	Intermediate Similarity	NPD6404	Discontinued
0.7113	Intermediate Similarity	NPD4623	Approved
0.7113	Intermediate Similarity	NPD4519	Discontinued
0.7111	Intermediate Similarity	NPD4784	Approved
0.7111	Intermediate Similarity	NPD4785	Approved
0.7111	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6411	Approved
0.7091	Intermediate Similarity	NPD5215	Approved
0.7091	Intermediate Similarity	NPD5217	Approved
0.7091	Intermediate Similarity	NPD5127	Approved
0.7091	Intermediate Similarity	NPD5216	Approved
0.7087	Intermediate Similarity	NPD5959	Approved
0.7075	Intermediate Similarity	NPD6052	Approved
0.7071	Intermediate Similarity	NPD7285	Clinical (unspecified phase)

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