NPASS Compound

Structure

NPC96496 OpenBabel07101718292D 34 37 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 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 -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 3.4641 3.7321 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 1 19 1 0 0 0 0 2 19 1 0 0 0 0 5 29 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 19 2 0 0 0 0 10 11 1 0 0 0 0 10 23 2 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 27 1 0 0 0 0 16 30 1 0 0 0 0 17 29 1 0 0 0 0 18 28 1 0 0 0 0 18 31 1 0 0 0 0 20 9 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 29 1 6 0 0 0 22 23 1 0 0 0 0 22 27 1 1 0 0 0 23 30 1 0 0 0 0 24 27 1 1 0 0 0 24 28 1 0 0 0 0 25 28 1 0 0 0 0 25 32 2 0 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 27 3 1 1 0 0 0 28 4 1 6 0 0 0 29 30 1 6 0 0 0 30 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	517.825
LogP:	6.133
LogD:	4.223
LogS:	-4.515
# Rotatable Bonds:	6
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	4.89
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.357
MDCK Permeability:	8.218075890908949e-06
Pgp-inhibitor:	0.253
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.85
30% Bioavailability (F30%):	0.798

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.39
Plasma Protein Binding (PPB):	92.85274505615234%
Volume Distribution (VD):	0.591
Pgp-substrate:	2.398493766784668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.296
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.358
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.447
CYP3A4-substrate:	0.483

ADMET: Excretion

Clearance (CL):	14.117
Half-life (T1/2):	0.328

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.493
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.692
Maximum Recommended Daily Dose:	0.468
Skin Sensitization:	0.116
Carcinogencity:	0.407
Eye Corrosion:	0.005
Eye Irritation:	0.047
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC96496

Natural Product ID:	NPC96496
*Common Name:**	Xanthocerasic Acid
IUPAC Name:	(2S)-2-[(4S,5R,9R,10R,13S,14S,17S)-4-(hydroxymethyl)-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:	xanthocerasic acid
Standard InCHIKey:	VOAKMNNRISZQAG-GJFGDYKQSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-19(2)8-7-9-20(26(33)34)21-12-16-30(6)23-10-11-24-27(3,22(23)13-17-29(21,30)5)15-14-25(32)28(24,4)18-31/h8,10,20-22,24,31H,7,9,11-18H2,1-6H3,(H,33,34)/t20-,21-,22-,24+,27+,28+,29-,30+/m0/s1
SMILES:	OC[C@@]1(C)C(=O)CC[C@]2([C@H]1CC=C1[C@@H]2CC[C@@]2([C@]1(C)CC[C@H]2[C@@H](C(=O)O)CCC=C(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516768
PubChem CID:	10695717
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[538940]
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	Inhibition	=	14.0	%	PMID[538940]

☑ 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 NPC96496 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	160
0.1-0.2	1032
0.2-0.3	5138
0.3-0.4	14624
0.4-0.5	7622
0.5-0.6	5965
0.6-0.7	5106
0.7-0.8	2578
0.8-0.85	361
0.85-0.9	99
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC474570
0.9268	High Similarity	NPC477373
0.9259	High Similarity	NPC147066
0.9167	High Similarity	NPC155011
0.908	High Similarity	NPC154101
0.907	High Similarity	NPC475921
0.907	High Similarity	NPC474704
0.9059	High Similarity	NPC474684
0.9059	High Similarity	NPC142361
0.9059	High Similarity	NPC173089
0.9059	High Similarity	NPC158141
0.9048	High Similarity	NPC201655
0.9024	High Similarity	NPC38350
0.9024	High Similarity	NPC201912
0.9012	High Similarity	NPC477371
0.8989	High Similarity	NPC263347
0.8953	High Similarity	NPC474511
0.8953	High Similarity	NPC328313
0.8953	High Similarity	NPC1753
0.8929	High Similarity	NPC82902
0.8929	High Similarity	NPC165064
0.8929	High Similarity	NPC221758
0.8929	High Similarity	NPC214043
0.8929	High Similarity	NPC85774
0.8929	High Similarity	NPC59453
0.8916	High Similarity	NPC260956
0.8916	High Similarity	NPC133391
0.8916	High Similarity	NPC320514
0.8889	High Similarity	NPC29152
0.8864	High Similarity	NPC212301
0.8864	High Similarity	NPC189520
0.8864	High Similarity	NPC86266
0.8864	High Similarity	NPC110657
0.8851	High Similarity	NPC215029
0.8851	High Similarity	NPC54689
0.8851	High Similarity	NPC476733
0.8837	High Similarity	NPC136948
0.8837	High Similarity	NPC187376
0.8837	High Similarity	NPC317590
0.8837	High Similarity	NPC159046
0.8837	High Similarity	NPC90652
0.8837	High Similarity	NPC233836
0.8824	High Similarity	NPC474218
0.8824	High Similarity	NPC469948
0.8824	High Similarity	NPC471224
0.8824	High Similarity	NPC29447
0.881	High Similarity	NPC83569
0.881	High Similarity	NPC69279
0.8795	High Similarity	NPC477372
0.8791	High Similarity	NPC156546
0.8778	High Similarity	NPC469599
0.8764	High Similarity	NPC66429
0.8764	High Similarity	NPC107674
0.8764	High Similarity	NPC152897
0.8764	High Similarity	NPC170220
0.8764	High Similarity	NPC141497
0.8764	High Similarity	NPC474807
0.8764	High Similarity	NPC470376
0.8764	High Similarity	NPC470375
0.875	High Similarity	NPC471896
0.8736	High Similarity	NPC53911
0.8736	High Similarity	NPC242864
0.8736	High Similarity	NPC470417
0.8721	High Similarity	NPC145879
0.8721	High Similarity	NPC474732
0.8721	High Similarity	NPC474778
0.8721	High Similarity	NPC28252
0.8721	High Similarity	NPC469994
0.8721	High Similarity	NPC31564
0.8721	High Similarity	NPC51014
0.8721	High Similarity	NPC55309
0.8721	High Similarity	NPC474733
0.8706	High Similarity	NPC237712
0.8706	High Similarity	NPC473246
0.8706	High Similarity	NPC476038
0.8706	High Similarity	NPC194937
0.869	High Similarity	NPC151519
0.8675	High Similarity	NPC472478
0.8667	High Similarity	NPC124207
0.8667	High Similarity	NPC49670
0.8659	High Similarity	NPC82635
0.8652	High Similarity	NPC6255
0.8652	High Similarity	NPC471588
0.8652	High Similarity	NPC297265
0.8636	High Similarity	NPC474700
0.8636	High Similarity	NPC84271
0.8636	High Similarity	NPC32830
0.8636	High Similarity	NPC31985
0.8636	High Similarity	NPC474245
0.8636	High Similarity	NPC1015
0.8636	High Similarity	NPC102414
0.8636	High Similarity	NPC262043
0.8636	High Similarity	NPC477943
0.8636	High Similarity	NPC77168
0.8621	High Similarity	NPC472481
0.8621	High Similarity	NPC472484
0.8621	High Similarity	NPC93778
0.8621	High Similarity	NPC475740
0.8621	High Similarity	NPC472482
0.8621	High Similarity	NPC312215
0.8621	High Similarity	NPC134197
0.8621	High Similarity	NPC58063
0.8621	High Similarity	NPC167877
0.8605	High Similarity	NPC474083
0.8605	High Similarity	NPC470223
0.8605	High Similarity	NPC283733
0.8588	High Similarity	NPC167103
0.8588	High Similarity	NPC168188
0.8588	High Similarity	NPC470015
0.8587	High Similarity	NPC475894
0.8587	High Similarity	NPC108078
0.8587	High Similarity	NPC57416
0.8587	High Similarity	NPC107243
0.8571	High Similarity	NPC476174
0.8571	High Similarity	NPC88310
0.8571	High Similarity	NPC278459
0.8556	High Similarity	NPC470224
0.8556	High Similarity	NPC206810
0.8556	High Similarity	NPC243866
0.8554	High Similarity	NPC215843
0.8554	High Similarity	NPC158846
0.8539	High Similarity	NPC175628
0.8539	High Similarity	NPC320026
0.8539	High Similarity	NPC148414
0.8539	High Similarity	NPC469400
0.8539	High Similarity	NPC111585
0.8539	High Similarity	NPC171441
0.8523	High Similarity	NPC294480
0.8523	High Similarity	NPC211162
0.8523	High Similarity	NPC183374
0.8523	High Similarity	NPC471724
0.8511	High Similarity	NPC472924
0.8506	High Similarity	NPC324063
0.8506	High Similarity	NPC70661
0.8506	High Similarity	NPC212843
0.8506	High Similarity	NPC473168
0.8506	High Similarity	NPC262085
0.8506	High Similarity	NPC73038
0.8506	High Similarity	NPC322159
0.8488	Intermediate Similarity	NPC161423
0.8488	Intermediate Similarity	NPC227064
0.8488	Intermediate Similarity	NPC58841
0.8488	Intermediate Similarity	NPC329043
0.8488	Intermediate Similarity	NPC321187
0.8478	Intermediate Similarity	NPC472941
0.8478	Intermediate Similarity	NPC155676
0.8478	Intermediate Similarity	NPC471153
0.8478	Intermediate Similarity	NPC327788
0.8478	Intermediate Similarity	NPC456
0.8478	Intermediate Similarity	NPC120708
0.8471	Intermediate Similarity	NPC240302
0.8462	Intermediate Similarity	NPC469406
0.8462	Intermediate Similarity	NPC474529
0.8462	Intermediate Similarity	NPC148964
0.8462	Intermediate Similarity	NPC159410
0.8462	Intermediate Similarity	NPC166906
0.8452	Intermediate Similarity	NPC104545
0.8452	Intermediate Similarity	NPC2482
0.8452	Intermediate Similarity	NPC37038
0.8444	Intermediate Similarity	NPC288833
0.8444	Intermediate Similarity	NPC26888
0.8444	Intermediate Similarity	NPC966
0.8444	Intermediate Similarity	NPC282616
0.8444	Intermediate Similarity	NPC23434
0.8444	Intermediate Similarity	NPC228784
0.8444	Intermediate Similarity	NPC155120
0.8444	Intermediate Similarity	NPC473998
0.8444	Intermediate Similarity	NPC324341
0.8434	Intermediate Similarity	NPC110094
0.8434	Intermediate Similarity	NPC260385
0.8434	Intermediate Similarity	NPC280654
0.8434	Intermediate Similarity	NPC321514
0.8427	Intermediate Similarity	NPC213832
0.8427	Intermediate Similarity	NPC214387
0.8427	Intermediate Similarity	NPC310010
0.8427	Intermediate Similarity	NPC326627
0.8427	Intermediate Similarity	NPC116146
0.8427	Intermediate Similarity	NPC76879
0.8427	Intermediate Similarity	NPC268406
0.8427	Intermediate Similarity	NPC57954
0.8427	Intermediate Similarity	NPC477973
0.8427	Intermediate Similarity	NPC474889
0.8427	Intermediate Similarity	NPC2983
0.8427	Intermediate Similarity	NPC26959
0.8427	Intermediate Similarity	NPC309603
0.8427	Intermediate Similarity	NPC281524
0.8427	Intermediate Similarity	NPC473999
0.8427	Intermediate Similarity	NPC24772
0.8427	Intermediate Similarity	NPC128496
0.8427	Intermediate Similarity	NPC186688
0.8415	Intermediate Similarity	NPC246445
0.8409	Intermediate Similarity	NPC128644
0.8404	Intermediate Similarity	NPC477521
0.8404	Intermediate Similarity	NPC167974
0.8404	Intermediate Similarity	NPC218383
0.8391	Intermediate Similarity	NPC94531
0.8391	Intermediate Similarity	NPC76333
0.8391	Intermediate Similarity	NPC123319
0.8391	Intermediate Similarity	NPC470574
0.8391	Intermediate Similarity	NPC311702

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 NPC96496 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	1344
0.2-0.3	3979
0.3-0.4	2490
0.4-0.5	648
0.5-0.6	225
0.6-0.7	111
0.7-0.8	165
0.8-0.85	39
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD4786	Approved
0.8764	High Similarity	NPD6399	Phase 3
0.869	High Similarity	NPD3667	Approved
0.8587	High Similarity	NPD6084	Phase 2
0.8587	High Similarity	NPD6083	Phase 2
0.8523	High Similarity	NPD5737	Approved
0.8523	High Similarity	NPD6672	Approved
0.8488	Intermediate Similarity	NPD3133	Approved
0.8488	Intermediate Similarity	NPD3666	Approved
0.8488	Intermediate Similarity	NPD3665	Phase 1
0.8427	Intermediate Similarity	NPD5328	Approved
0.8427	Intermediate Similarity	NPD4753	Phase 2
0.8295	Intermediate Similarity	NPD3618	Phase 1
0.8295	Intermediate Similarity	NPD7521	Approved
0.8295	Intermediate Similarity	NPD7334	Approved
0.8295	Intermediate Similarity	NPD6409	Approved
0.8295	Intermediate Similarity	NPD6684	Approved
0.8295	Intermediate Similarity	NPD7146	Approved
0.8295	Intermediate Similarity	NPD5330	Approved
0.8256	Intermediate Similarity	NPD4223	Phase 3
0.8256	Intermediate Similarity	NPD4221	Approved
0.8242	Intermediate Similarity	NPD7515	Phase 2
0.8242	Intermediate Similarity	NPD6079	Approved
0.8182	Intermediate Similarity	NPD5329	Approved
0.8182	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8172	Intermediate Similarity	NPD5695	Phase 3
0.8111	Intermediate Similarity	NPD6903	Approved
0.8111	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD5696	Approved
0.809	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD5279	Phase 3
0.809	Intermediate Similarity	NPD6098	Approved
0.8068	Intermediate Similarity	NPD4197	Approved
0.8068	Intermediate Similarity	NPD3668	Phase 3
0.8043	Intermediate Similarity	NPD5281	Approved
0.8043	Intermediate Similarity	NPD5284	Approved
0.8022	Intermediate Similarity	NPD6673	Approved
0.8022	Intermediate Similarity	NPD6080	Approved
0.8022	Intermediate Similarity	NPD6904	Approved
0.798	Intermediate Similarity	NPD7128	Approved
0.798	Intermediate Similarity	NPD6402	Approved
0.798	Intermediate Similarity	NPD5739	Approved
0.798	Intermediate Similarity	NPD6675	Approved
0.7979	Intermediate Similarity	NPD5210	Approved
0.7979	Intermediate Similarity	NPD4629	Approved
0.7957	Intermediate Similarity	NPD4202	Approved
0.7955	Intermediate Similarity	NPD4788	Approved
0.7895	Intermediate Similarity	NPD5222	Approved
0.7895	Intermediate Similarity	NPD4697	Phase 3
0.7895	Intermediate Similarity	NPD5221	Approved
0.7895	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD4693	Phase 3
0.7889	Intermediate Similarity	NPD4690	Approved
0.7889	Intermediate Similarity	NPD4689	Approved
0.7889	Intermediate Similarity	NPD4688	Approved
0.7889	Intermediate Similarity	NPD4138	Approved
0.7889	Intermediate Similarity	NPD5205	Approved
0.7872	Intermediate Similarity	NPD7748	Approved
0.7857	Intermediate Similarity	NPD6942	Approved
0.7857	Intermediate Similarity	NPD7339	Approved
0.7822	Intermediate Similarity	NPD6899	Approved
0.7822	Intermediate Similarity	NPD6881	Approved
0.7822	Intermediate Similarity	NPD7320	Approved
0.7812	Intermediate Similarity	NPD4755	Approved
0.7812	Intermediate Similarity	NPD5173	Approved
0.7791	Intermediate Similarity	NPD3617	Approved
0.7791	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD6372	Approved
0.7745	Intermediate Similarity	NPD6373	Approved
0.7723	Intermediate Similarity	NPD5697	Approved
0.7723	Intermediate Similarity	NPD5701	Approved
0.7717	Intermediate Similarity	NPD5208	Approved
0.7692	Intermediate Similarity	NPD4694	Approved
0.7692	Intermediate Similarity	NPD5690	Phase 2
0.7692	Intermediate Similarity	NPD5280	Approved
0.767	Intermediate Similarity	NPD6883	Approved
0.767	Intermediate Similarity	NPD7102	Approved
0.767	Intermediate Similarity	NPD7290	Approved
0.766	Intermediate Similarity	NPD6050	Approved
0.766	Intermediate Similarity	NPD6411	Approved
0.766	Intermediate Similarity	NPD5693	Phase 1
0.766	Intermediate Similarity	NPD8034	Phase 2
0.766	Intermediate Similarity	NPD8035	Phase 2
0.7653	Intermediate Similarity	NPD5285	Approved
0.7653	Intermediate Similarity	NPD4700	Approved
0.7653	Intermediate Similarity	NPD5286	Approved
0.7653	Intermediate Similarity	NPD4696	Approved
0.7647	Intermediate Similarity	NPD6011	Approved
0.7634	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7902	Approved
0.7614	Intermediate Similarity	NPD7525	Registered
0.7614	Intermediate Similarity	NPD4695	Discontinued
0.7596	Intermediate Similarity	NPD6649	Approved
0.7596	Intermediate Similarity	NPD8130	Phase 1
0.7596	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6847	Approved
0.7596	Intermediate Similarity	NPD6650	Approved
0.7596	Intermediate Similarity	NPD6617	Approved
0.7596	Intermediate Similarity	NPD6869	Approved
0.759	Intermediate Similarity	NPD4747	Approved
0.7576	Intermediate Similarity	NPD5223	Approved
0.7573	Intermediate Similarity	NPD6012	Approved
0.7573	Intermediate Similarity	NPD6014	Approved
0.7573	Intermediate Similarity	NPD6013	Approved
0.757	Intermediate Similarity	NPD7115	Discovery
0.7558	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6117	Approved
0.7553	Intermediate Similarity	NPD5692	Phase 3
0.7551	Intermediate Similarity	NPD7638	Approved
0.7529	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4692	Approved
0.7528	Intermediate Similarity	NPD5369	Approved
0.7528	Intermediate Similarity	NPD4139	Approved
0.7524	Intermediate Similarity	NPD6882	Approved
0.7524	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD5211	Phase 2
0.75	Intermediate Similarity	NPD4243	Approved
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD6081	Approved
0.75	Intermediate Similarity	NPD4195	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.7475	Intermediate Similarity	NPD7640	Approved
0.7475	Intermediate Similarity	NPD7639	Approved
0.7474	Intermediate Similarity	NPD5694	Approved
0.7474	Intermediate Similarity	NPD7637	Suspended
0.7471	Intermediate Similarity	NPD6116	Phase 1
0.747	Intermediate Similarity	NPD4137	Phase 3
0.7447	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6101	Approved
0.7444	Intermediate Similarity	NPD4270	Approved
0.7444	Intermediate Similarity	NPD4269	Approved
0.7426	Intermediate Similarity	NPD5174	Approved
0.7426	Intermediate Similarity	NPD5175	Approved
0.7426	Intermediate Similarity	NPD4754	Approved
0.7407	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6115	Approved
0.7386	Intermediate Similarity	NPD6118	Approved
0.7386	Intermediate Similarity	NPD6114	Approved
0.7386	Intermediate Similarity	NPD6697	Approved
0.7381	Intermediate Similarity	NPD4691	Approved
0.7381	Intermediate Similarity	NPD4789	Approved
0.7379	Intermediate Similarity	NPD6412	Phase 2
0.7368	Intermediate Similarity	NPD5207	Approved
0.7353	Intermediate Similarity	NPD5141	Approved
0.7349	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4634	Approved
0.7326	Intermediate Similarity	NPD6926	Approved
0.7326	Intermediate Similarity	NPD6924	Approved
0.7326	Intermediate Similarity	NPD4784	Approved
0.7326	Intermediate Similarity	NPD5733	Approved
0.7326	Intermediate Similarity	NPD4785	Approved
0.732	Intermediate Similarity	NPD7900	Approved
0.732	Intermediate Similarity	NPD6001	Approved
0.732	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4224	Phase 2
0.7315	Intermediate Similarity	NPD6868	Approved
0.7312	Intermediate Similarity	NPD4623	Approved
0.7312	Intermediate Similarity	NPD4519	Discontinued
0.7294	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4632	Approved
0.7282	Intermediate Similarity	NPD4768	Approved
0.7282	Intermediate Similarity	NPD4767	Approved
0.7263	Intermediate Similarity	NPD6051	Approved
0.7253	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5368	Approved
0.7222	Intermediate Similarity	NPD4252	Approved
0.7207	Intermediate Similarity	NPD6319	Approved
0.7204	Intermediate Similarity	NPD5363	Approved
0.7188	Intermediate Similarity	NPD5785	Approved
0.7188	Intermediate Similarity	NPD4096	Approved
0.7182	Intermediate Similarity	NPD6335	Approved
0.7176	Intermediate Similarity	NPD4245	Approved
0.7176	Intermediate Similarity	NPD4244	Approved
0.7174	Intermediate Similarity	NPD5362	Discontinued
0.7172	Intermediate Similarity	NPD7614	Phase 1
0.7159	Intermediate Similarity	NPD6933	Approved
0.7156	Intermediate Similarity	NPD6274	Approved
0.7143	Intermediate Similarity	NPD5128	Approved
0.7143	Intermediate Similarity	NPD4730	Approved
0.7143	Intermediate Similarity	NPD5168	Approved
0.7143	Intermediate Similarity	NPD4729	Approved
0.7129	Intermediate Similarity	NPD6404	Discontinued
0.7128	Intermediate Similarity	NPD5786	Approved
0.7126	Intermediate Similarity	NPD4058	Approved
0.7126	Intermediate Similarity	NPD4687	Approved
0.7117	Intermediate Similarity	NPD7100	Approved
0.7117	Intermediate Similarity	NPD7101	Approved
0.7115	Intermediate Similarity	NPD6008	Approved
0.7105	Intermediate Similarity	NPD7492	Approved
0.7093	Intermediate Similarity	NPD5276	Approved
0.7091	Intermediate Similarity	NPD6009	Approved
0.7091	Intermediate Similarity	NPD6317	Approved
0.7087	Intermediate Similarity	NPD6052	Approved
0.7071	Intermediate Similarity	NPD5654	Approved
0.7065	Intermediate Similarity	NPD6435	Approved
0.7059	Intermediate Similarity	NPD3699	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