NPASS Compound

Structure

NPC474570 OpenBabel07101718192D 37 40 0 0 1 0 0 0 0 0999 V2000 4.8126 4.7859 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 -4.9641 -2.8660 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 -3.9641 -2.8660 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 2.5472 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5254 3.6270 0.0000 C 0 0 0 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 -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 1.5388 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 -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 0.9511 -0.3090 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 -2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8344 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4641 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 1 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 -1.7321 0.0000 0.0000 C 0 0 1 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 -2.5981 -1.5000 0.0000 C 0 0 2 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 0.5909 3.0032 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 -3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 -4.9641 -4.5981 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 0.9000 3.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3872 2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 6 31 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 20 2 0 0 0 0 11 12 1 0 0 0 0 11 25 2 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 29 1 0 0 0 0 17 32 1 0 0 0 0 18 31 1 0 0 0 0 19 30 1 0 0 0 0 19 37 1 0 0 0 0 21 33 2 0 0 0 0 21 37 1 0 0 0 0 22 10 1 1 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 31 1 6 0 0 0 24 25 1 0 0 0 0 24 29 1 1 0 0 0 25 32 1 0 0 0 0 26 29 1 1 0 0 0 26 30 1 0 0 0 0 27 30 1 0 0 0 0 27 34 2 0 0 0 0 28 35 2 0 0 0 0 28 36 1 0 0 0 0 29 4 1 1 0 0 0 30 5 1 6 0 0 0 31 32 1 6 0 0 0 32 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.35
Volume:	558.571
LogP:	6.564
LogD:	4.639
LogS:	-4.768
# Rotatable Bonds:	8
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.289
Synthetic Accessibility Score:	4.945
Fsp3:	0.781
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:	-5.389
MDCK Permeability:	1.214192798215663e-05
Pgp-inhibitor:	0.718
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.709
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.236
Plasma Protein Binding (PPB):	93.38091278076172%
Volume Distribution (VD):	0.626
Pgp-substrate:	2.4149272441864014%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.192
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.876
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.447
CYP3A4-substrate:	0.527

ADMET: Excretion

Clearance (CL):	7.339
Half-life (T1/2):	0.317

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.086
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.533
Maximum Recommended Daily Dose:	0.509
Skin Sensitization:	0.111
Carcinogencity:	0.396
Eye Corrosion:	0.008
Eye Irritation:	0.122
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC474570

Natural Product ID:	NPC474570
*Common Name:**	29-O-Acetyl-3-Oxotirucalla-7,24-Dien-21-Oic Acid
IUPAC Name:	(2S)-2-[(4S,5R,9R,10R,13S,14S,17S)-4-(acetyloxymethyl)-4,10,13,14-tetramethyl-3-oxo-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms:
Standard InCHIKey:	WNBQUUXWPDCLBL-SURDOKLXSA-N
Standard InCHI:	InChI=1S/C32H48O5/c1-20(2)9-8-10-22(28(35)36)23-13-17-32(7)25-11-12-26-29(4,24(25)14-18-31(23,32)6)16-15-27(34)30(26,5)19-37-21(3)33/h9,11,22-24,26H,8,10,12-19H2,1-7H3,(H,35,36)/t22-,23-,24-,26+,29+,30+,31-,32+/m0/s1
SMILES:	CC(=CCCC(C1CCC2(C1(CCC3C2=CCC4C3(CCC(=O)C4(C)COC(=O)C)C)C)C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL474062
PubChem CID:	10529766
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
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	wood	n.a.	n.a.	PMID[10691716]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	husks	Inner Mongolia, China	2004-SEP	PMID[18549275]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22801644]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23313635]

☑ 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
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	IC50	>	100.0	ug.mL-1	PMID[509494]
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	Inhibition	=	26.0	%	PMID[509494]

☑ 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 NPC474570 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	166
0.1-0.2	1008
0.2-0.3	5027
0.3-0.4	13934
0.4-0.5	8094
0.5-0.6	5943
0.6-0.7	5482
0.7-0.8	2696
0.8-0.85	296
0.85-0.9	46
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC96496
0.9195	High Similarity	NPC471896
0.9048	High Similarity	NPC477373
0.9036	High Similarity	NPC147066
0.8977	High Similarity	NPC111585
0.8977	High Similarity	NPC148414
0.8977	High Similarity	NPC175628
0.8901	High Similarity	NPC327788
0.8889	High Similarity	NPC159410
0.8889	High Similarity	NPC124207
0.8876	High Similarity	NPC154101
0.8876	High Similarity	NPC26888
0.8864	High Similarity	NPC474700
0.8864	High Similarity	NPC474889
0.8851	High Similarity	NPC167877
0.8837	High Similarity	NPC470223
0.881	High Similarity	NPC327002
0.881	High Similarity	NPC201912
0.881	High Similarity	NPC38350
0.8795	High Similarity	NPC327674
0.8795	High Similarity	NPC477371
0.8791	High Similarity	NPC469599
0.8736	High Similarity	NPC264127
0.8736	High Similarity	NPC155011
0.8706	High Similarity	NPC320514
0.8706	High Similarity	NPC133391
0.8706	High Similarity	NPC260956
0.8706	High Similarity	NPC240302
0.8696	High Similarity	NPC120708
0.8652	High Similarity	NPC476733
0.8652	High Similarity	NPC475921
0.8652	High Similarity	NPC474704
0.8652	High Similarity	NPC215029
0.8636	High Similarity	NPC474684
0.8636	High Similarity	NPC136948
0.8636	High Similarity	NPC142361
0.8636	High Similarity	NPC158141
0.8636	High Similarity	NPC173089
0.8621	High Similarity	NPC76333
0.8621	High Similarity	NPC29447
0.8621	High Similarity	NPC201655
0.8617	High Similarity	NPC167974
0.8605	High Similarity	NPC83569
0.8605	High Similarity	NPC69279
0.8602	High Similarity	NPC475894
0.8588	High Similarity	NPC477372
0.8587	High Similarity	NPC473648
0.8587	High Similarity	NPC279974
0.8587	High Similarity	NPC263347
0.8571	High Similarity	NPC470224
0.8571	High Similarity	NPC170220
0.8571	High Similarity	NPC107674
0.8571	High Similarity	NPC141497
0.8539	High Similarity	NPC472220
0.8539	High Similarity	NPC28227
0.8539	High Similarity	NPC1753
0.8539	High Similarity	NPC474511
0.8539	High Similarity	NPC97884
0.8539	High Similarity	NPC328313
0.8526	High Similarity	NPC473514
0.8523	High Similarity	NPC325594
0.8523	High Similarity	NPC195640
0.8506	High Similarity	NPC100391
0.8506	High Similarity	NPC82902
0.8506	High Similarity	NPC59453
0.8506	High Similarity	NPC85774
0.8506	High Similarity	NPC214043
0.8506	High Similarity	NPC221758
0.8506	High Similarity	NPC165064
0.8495	Intermediate Similarity	NPC42042
0.8495	Intermediate Similarity	NPC29152
0.8488	Intermediate Similarity	NPC296367
0.8478	Intermediate Similarity	NPC78580
0.8478	Intermediate Similarity	NPC184006
0.8478	Intermediate Similarity	NPC23621
0.8471	Intermediate Similarity	NPC477057
0.8471	Intermediate Similarity	NPC104545
0.8469	Intermediate Similarity	NPC220974
0.8462	Intermediate Similarity	NPC471901
0.8462	Intermediate Similarity	NPC297265
0.8462	Intermediate Similarity	NPC86266
0.8462	Intermediate Similarity	NPC212301
0.8462	Intermediate Similarity	NPC110657
0.8462	Intermediate Similarity	NPC470113
0.8462	Intermediate Similarity	NPC189520
0.8452	Intermediate Similarity	NPC321514
0.8444	Intermediate Similarity	NPC54689
0.8444	Intermediate Similarity	NPC262043
0.8438	Intermediate Similarity	NPC473928
0.8427	Intermediate Similarity	NPC159046
0.8427	Intermediate Similarity	NPC90652
0.8427	Intermediate Similarity	NPC233836
0.8427	Intermediate Similarity	NPC134197
0.8427	Intermediate Similarity	NPC187376
0.8427	Intermediate Similarity	NPC128644
0.8427	Intermediate Similarity	NPC317590
0.8421	Intermediate Similarity	NPC477521
0.8409	Intermediate Similarity	NPC469948
0.8409	Intermediate Similarity	NPC283733
0.8409	Intermediate Similarity	NPC323765
0.8409	Intermediate Similarity	NPC471224
0.8409	Intermediate Similarity	NPC474218
0.8404	Intermediate Similarity	NPC26413
0.8404	Intermediate Similarity	NPC57416
0.8404	Intermediate Similarity	NPC107243
0.8404	Intermediate Similarity	NPC156546
0.8391	Intermediate Similarity	NPC471037
0.8391	Intermediate Similarity	NPC200752
0.8391	Intermediate Similarity	NPC167103
0.8391	Intermediate Similarity	NPC168188
0.8391	Intermediate Similarity	NPC470015
0.8387	Intermediate Similarity	NPC195715
0.8387	Intermediate Similarity	NPC69548
0.8387	Intermediate Similarity	NPC184848
0.8387	Intermediate Similarity	NPC23241
0.8372	Intermediate Similarity	NPC278459
0.837	Intermediate Similarity	NPC474807
0.837	Intermediate Similarity	NPC287118
0.837	Intermediate Similarity	NPC473690
0.837	Intermediate Similarity	NPC169343
0.837	Intermediate Similarity	NPC152897
0.837	Intermediate Similarity	NPC470375
0.837	Intermediate Similarity	NPC470376
0.837	Intermediate Similarity	NPC471902
0.837	Intermediate Similarity	NPC66429
0.8353	Intermediate Similarity	NPC215843
0.8353	Intermediate Similarity	NPC158846
0.8352	Intermediate Similarity	NPC113989
0.8352	Intermediate Similarity	NPC120840
0.8333	Intermediate Similarity	NPC56413
0.8333	Intermediate Similarity	NPC183546
0.8333	Intermediate Similarity	NPC474327
0.8333	Intermediate Similarity	NPC294480
0.8333	Intermediate Similarity	NPC242864
0.8333	Intermediate Similarity	NPC470417
0.8333	Intermediate Similarity	NPC53911
0.8333	Intermediate Similarity	NPC99411
0.8333	Intermediate Similarity	NPC4309
0.8316	Intermediate Similarity	NPC477813
0.8316	Intermediate Similarity	NPC119036
0.8315	Intermediate Similarity	NPC145879
0.8315	Intermediate Similarity	NPC28252
0.8315	Intermediate Similarity	NPC73038
0.8315	Intermediate Similarity	NPC31564
0.8315	Intermediate Similarity	NPC262085
0.8315	Intermediate Similarity	NPC469994
0.8315	Intermediate Similarity	NPC51014
0.8315	Intermediate Similarity	NPC324063
0.8315	Intermediate Similarity	NPC474733
0.8315	Intermediate Similarity	NPC322159
0.8315	Intermediate Similarity	NPC474970
0.8315	Intermediate Similarity	NPC55309
0.8315	Intermediate Similarity	NPC474732
0.8315	Intermediate Similarity	NPC474778
0.8298	Intermediate Similarity	NPC322063
0.8298	Intermediate Similarity	NPC471153
0.8295	Intermediate Similarity	NPC156981
0.8295	Intermediate Similarity	NPC237712
0.8295	Intermediate Similarity	NPC473246
0.8295	Intermediate Similarity	NPC476038
0.8295	Intermediate Similarity	NPC194937
0.8295	Intermediate Similarity	NPC312660
0.828	Intermediate Similarity	NPC74751
0.828	Intermediate Similarity	NPC473280
0.828	Intermediate Similarity	NPC473435
0.828	Intermediate Similarity	NPC174051
0.828	Intermediate Similarity	NPC49670
0.828	Intermediate Similarity	NPC471078
0.828	Intermediate Similarity	NPC473431
0.828	Intermediate Similarity	NPC67831
0.8276	Intermediate Similarity	NPC100297
0.8276	Intermediate Similarity	NPC327969
0.8276	Intermediate Similarity	NPC151519
0.8276	Intermediate Similarity	NPC321289
0.8261	Intermediate Similarity	NPC474018
0.8261	Intermediate Similarity	NPC470590
0.8261	Intermediate Similarity	NPC471588
0.8261	Intermediate Similarity	NPC475416
0.8261	Intermediate Similarity	NPC218301
0.8261	Intermediate Similarity	NPC77099
0.8261	Intermediate Similarity	NPC60755
0.8261	Intermediate Similarity	NPC6255
0.8261	Intermediate Similarity	NPC285184
0.8261	Intermediate Similarity	NPC473986
0.8261	Intermediate Similarity	NPC262870
0.8261	Intermediate Similarity	NPC150383
0.8256	Intermediate Similarity	NPC472478
0.8256	Intermediate Similarity	NPC37038
0.8247	Intermediate Similarity	NPC22388
0.8247	Intermediate Similarity	NPC475558
0.8247	Intermediate Similarity	NPC473788
0.8242	Intermediate Similarity	NPC77168
0.8242	Intermediate Similarity	NPC31985
0.8242	Intermediate Similarity	NPC1015
0.8242	Intermediate Similarity	NPC30522
0.8242	Intermediate Similarity	NPC32830
0.8242	Intermediate Similarity	NPC305039
0.8242	Intermediate Similarity	NPC84271
0.8242	Intermediate Similarity	NPC102414
0.8242	Intermediate Similarity	NPC477943

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 NPC474570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1290
0.2-0.3	4011
0.3-0.4	2493
0.4-0.5	653
0.5-0.6	229
0.6-0.7	141
0.7-0.8	152
0.8-0.85	27
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8989	High Similarity	NPD6399	Phase 3
0.875	High Similarity	NPD6672	Approved
0.875	High Similarity	NPD5737	Approved
0.8602	High Similarity	NPD6084	Phase 2
0.8602	High Similarity	NPD6083	Phase 2
0.8523	High Similarity	NPD6684	Approved
0.8523	High Similarity	NPD7146	Approved
0.8523	High Similarity	NPD7521	Approved
0.8523	High Similarity	NPD5330	Approved
0.8523	High Similarity	NPD7334	Approved
0.8523	High Similarity	NPD6409	Approved
0.8506	High Similarity	NPD4786	Approved
0.8387	Intermediate Similarity	NPD5695	Phase 3
0.8333	Intermediate Similarity	NPD6903	Approved
0.8333	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8316	Intermediate Similarity	NPD5696	Approved
0.8315	Intermediate Similarity	NPD6098	Approved
0.828	Intermediate Similarity	NPD7748	Approved
0.8276	Intermediate Similarity	NPD3667	Approved
0.8242	Intermediate Similarity	NPD6904	Approved
0.8242	Intermediate Similarity	NPD6673	Approved
0.8242	Intermediate Similarity	NPD6080	Approved
0.809	Intermediate Similarity	NPD3666	Approved
0.809	Intermediate Similarity	NPD3665	Phase 1
0.809	Intermediate Similarity	NPD3133	Approved
0.8068	Intermediate Similarity	NPD4221	Approved
0.8068	Intermediate Similarity	NPD4223	Phase 3
0.8065	Intermediate Similarity	NPD8034	Phase 2
0.8065	Intermediate Similarity	NPD8035	Phase 2
0.8043	Intermediate Similarity	NPD4753	Phase 2
0.8043	Intermediate Similarity	NPD5328	Approved
0.8021	Intermediate Similarity	NPD7902	Approved
0.8	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5329	Approved
0.8	Intermediate Similarity	NPD6675	Approved
0.8	Intermediate Similarity	NPD5739	Approved
0.8	Intermediate Similarity	NPD7128	Approved
0.7935	Intermediate Similarity	NPD5208	Approved
0.7912	Intermediate Similarity	NPD3618	Phase 1
0.7912	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD3668	Phase 3
0.7889	Intermediate Similarity	NPD4197	Approved
0.7872	Intermediate Similarity	NPD5281	Approved
0.7872	Intermediate Similarity	NPD5284	Approved
0.7872	Intermediate Similarity	NPD5693	Phase 1
0.7872	Intermediate Similarity	NPD6079	Approved
0.7872	Intermediate Similarity	NPD6050	Approved
0.7872	Intermediate Similarity	NPD7515	Phase 2
0.7843	Intermediate Similarity	NPD6899	Approved
0.7843	Intermediate Similarity	NPD7320	Approved
0.7843	Intermediate Similarity	NPD6881	Approved
0.7802	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD8130	Phase 1
0.7767	Intermediate Similarity	NPD6372	Approved
0.7767	Intermediate Similarity	NPD6373	Approved
0.7766	Intermediate Similarity	NPD5692	Phase 3
0.7745	Intermediate Similarity	NPD5701	Approved
0.7745	Intermediate Similarity	NPD5697	Approved
0.7717	Intermediate Similarity	NPD4690	Approved
0.7717	Intermediate Similarity	NPD5205	Approved
0.7717	Intermediate Similarity	NPD5279	Phase 3
0.7717	Intermediate Similarity	NPD4138	Approved
0.7717	Intermediate Similarity	NPD4688	Approved
0.7717	Intermediate Similarity	NPD4689	Approved
0.7717	Intermediate Similarity	NPD4693	Phase 3
0.7714	Intermediate Similarity	NPD8297	Approved
0.7708	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD7900	Approved
0.7692	Intermediate Similarity	NPD7102	Approved
0.7692	Intermediate Similarity	NPD6883	Approved
0.7692	Intermediate Similarity	NPD7290	Approved
0.7684	Intermediate Similarity	NPD5694	Approved
0.7684	Intermediate Similarity	NPD6411	Approved
0.767	Intermediate Similarity	NPD6011	Approved
0.7629	Intermediate Similarity	NPD4629	Approved
0.7629	Intermediate Similarity	NPD5210	Approved
0.7619	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6869	Approved
0.7619	Intermediate Similarity	NPD6649	Approved
0.7619	Intermediate Similarity	NPD6847	Approved
0.7619	Intermediate Similarity	NPD6617	Approved
0.7619	Intermediate Similarity	NPD6650	Approved
0.7614	Intermediate Similarity	NPD3617	Approved
0.7604	Intermediate Similarity	NPD4202	Approved
0.7596	Intermediate Similarity	NPD6013	Approved
0.7596	Intermediate Similarity	NPD6012	Approved
0.7596	Intermediate Similarity	NPD6014	Approved
0.7593	Intermediate Similarity	NPD7115	Discovery
0.7582	Intermediate Similarity	NPD4788	Approved
0.7579	Intermediate Similarity	NPD5207	Approved
0.7576	Intermediate Similarity	NPD7638	Approved
0.7551	Intermediate Similarity	NPD5222	Approved
0.7551	Intermediate Similarity	NPD4697	Phase 3
0.7551	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5221	Approved
0.7547	Intermediate Similarity	NPD6882	Approved
0.7527	Intermediate Similarity	NPD4694	Approved
0.7527	Intermediate Similarity	NPD5690	Phase 2
0.7527	Intermediate Similarity	NPD5280	Approved
0.7526	Intermediate Similarity	NPD6001	Approved
0.75	Intermediate Similarity	NPD7637	Suspended
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7475	Intermediate Similarity	NPD4755	Approved
0.7475	Intermediate Similarity	NPD5173	Approved
0.7474	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6101	Approved
0.7474	Intermediate Similarity	NPD6051	Approved
0.7474	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6942	Approved
0.7471	Intermediate Similarity	NPD7339	Approved
0.7444	Intermediate Similarity	NPD4695	Discontinued
0.7416	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4747	Approved
0.7404	Intermediate Similarity	NPD6412	Phase 2
0.7363	Intermediate Similarity	NPD4139	Approved
0.7363	Intermediate Similarity	NPD4692	Approved
0.7363	Intermediate Similarity	NPD5369	Approved
0.7339	Intermediate Similarity	NPD6868	Approved
0.7333	Intermediate Similarity	NPD4195	Approved
0.7327	Intermediate Similarity	NPD5285	Approved
0.7327	Intermediate Similarity	NPD5286	Approved
0.7327	Intermediate Similarity	NPD4700	Approved
0.7327	Intermediate Similarity	NPD4696	Approved
0.7326	Intermediate Similarity	NPD6081	Approved
0.7326	Intermediate Similarity	NPD4243	Approved
0.7308	Intermediate Similarity	NPD6008	Approved
0.7294	Intermediate Similarity	NPD4137	Phase 3
0.7282	Intermediate Similarity	NPD6052	Approved
0.7273	Intermediate Similarity	NPD5654	Approved
0.7273	Intermediate Similarity	NPD3702	Approved
0.7263	Intermediate Similarity	NPD3573	Approved
0.7255	Intermediate Similarity	NPD5223	Approved
0.7253	Intermediate Similarity	NPD7525	Registered
0.7232	Intermediate Similarity	NPD6319	Approved
0.7209	Intermediate Similarity	NPD4691	Approved
0.7207	Intermediate Similarity	NPD6335	Approved
0.7191	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6117	Approved
0.7184	Intermediate Similarity	NPD5211	Phase 2
0.7184	Intermediate Similarity	NPD5226	Approved
0.7184	Intermediate Similarity	NPD4633	Approved
0.7184	Intermediate Similarity	NPD5225	Approved
0.7184	Intermediate Similarity	NPD5224	Approved
0.7182	Intermediate Similarity	NPD6274	Approved
0.7176	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5733	Approved
0.7159	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4785	Approved
0.7159	Intermediate Similarity	NPD4784	Approved
0.7158	Intermediate Similarity	NPD4623	Approved
0.7158	Intermediate Similarity	NPD4519	Discontinued
0.7156	Intermediate Similarity	NPD4632	Approved
0.7155	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD4224	Phase 2
0.7143	Intermediate Similarity	NPD7100	Approved
0.7143	Intermediate Similarity	NPD7101	Approved
0.713	Intermediate Similarity	NPD7492	Approved
0.7129	Intermediate Similarity	NPD5959	Approved
0.7126	Intermediate Similarity	NPD5777	Approved
0.7117	Intermediate Similarity	NPD6317	Approved
0.7115	Intermediate Similarity	NPD5174	Approved
0.7115	Intermediate Similarity	NPD5175	Approved
0.7115	Intermediate Similarity	NPD4754	Approved
0.7111	Intermediate Similarity	NPD6116	Phase 1
0.7097	Intermediate Similarity	NPD4269	Approved
0.7097	Intermediate Similarity	NPD6435	Approved
0.7097	Intermediate Similarity	NPD4270	Approved
0.7094	Intermediate Similarity	NPD7736	Approved
0.708	Intermediate Similarity	NPD6059	Approved
0.708	Intermediate Similarity	NPD6054	Approved
0.7075	Intermediate Similarity	NPD6614	Approved
0.7071	Intermediate Similarity	NPD5778	Approved
0.7071	Intermediate Similarity	NPD5779	Approved
0.7069	Intermediate Similarity	NPD6616	Approved
0.7054	Intermediate Similarity	NPD6314	Approved
0.7054	Intermediate Similarity	NPD6313	Approved
0.7048	Intermediate Similarity	NPD5141	Approved
0.7041	Intermediate Similarity	NPD5785	Approved
0.7041	Intermediate Similarity	NPD4096	Approved
0.7037	Intermediate Similarity	NPD4634	Approved
0.7033	Intermediate Similarity	NPD6697	Approved
0.7033	Intermediate Similarity	NPD6115	Approved
0.7033	Intermediate Similarity	NPD6118	Approved
0.7033	Intermediate Similarity	NPD6114	Approved
0.703	Intermediate Similarity	NPD7614	Phase 1
0.703	Intermediate Similarity	NPD7732	Phase 3
0.7024	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5362	Discontinued
0.7018	Intermediate Similarity	NPD6909	Approved
0.7018	Intermediate Similarity	NPD6908	Approved
0.7011	Intermediate Similarity	NPD4789	Approved
0.7009	Intermediate Similarity	NPD7078	Approved
0.699	Remote Similarity	NPD6404	Discontinued
0.6981	Remote Similarity	NPD4768	Approved
0.6981	Remote Similarity	NPD4767	Approved
0.6979	Remote Similarity	NPD5786	Approved
0.6966	Remote Similarity	NPD4687	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