NPASS Compound

Structure

NPC264954 OpenBabel07101718322D 35 40 0 0 1 0 0 0 0 0999 V2000 8.1344 3.0743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6085 -0.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 1.9781 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 4.6665 2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9754 1.7872 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 9.6206 1.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9264 2.0962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8164 0.5000 0.0000 C 0 0 2 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 8.6696 1.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 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 6.7675 0.8090 0.0000 C 0 0 2 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 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4617 0.4489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0733 1.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3638 1.0669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2048 -0.2202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0243 1.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5106 0.1399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 6 2 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 9 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 25 1 0 0 0 0 10 27 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 29 1 0 0 0 0 14 17 2 0 0 0 0 15 2 1 1 0 0 0 15 27 1 0 0 0 0 16 12 1 1 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 6 0 0 0 19 26 1 6 0 0 0 20 15 1 1 0 0 0 20 34 1 0 0 0 0 21 26 1 0 0 0 0 21 30 2 0 0 0 0 22 28 1 6 0 0 0 22 31 1 0 0 0 0 23 28 1 1 0 0 0 23 35 1 0 0 0 0 24 32 2 0 0 0 0 24 34 1 0 0 0 0 25 27 1 1 0 0 0 26 28 1 6 0 0 0 27 33 1 1 0 0 0 28 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.26
Volume:	492.491
LogP:	2.577
LogD:	2.354
LogS:	-4.345
# Rotatable Bonds:	3
TPSA:	113.43
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	5.921
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.221
MDCK Permeability:	1.6034018699428998e-05
Pgp-inhibitor:	0.89
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.06
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.804
Plasma Protein Binding (PPB):	59.815704345703125%
Volume Distribution (VD):	0.466
Pgp-substrate:	16.71221160888672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.642
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.757
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	13.343
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.094
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.373
AMES Toxicity:	0.091
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.798
Skin Sensitization:	0.782
Carcinogencity:	0.774
Eye Corrosion:	0.014
Eye Irritation:	0.076
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC264954

Natural Product ID:	NPC264954
*Common Name:**	HLZVPWRVYKJCMY-ZHLLBWASSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HLZVPWRVYKJCMY-ZHLLBWASSA-N
Standard InCHI:	InChI=1S/C28H38O7/c1-14-11-20(34-24(32)17(14)13-29)15(2)27(33)10-8-18-16-12-23-28(35-23)22(31)6-5-21(30)26(28,4)19(16)7-9-25(18,27)3/h5-6,15-16,18-20,22-23,29,31,33H,7-13H2,1-4H3/t15-,16+,18+,19+,20-,22+,23-,25+,26+,27+,28-/m1/s1
SMILES:	OCC1=C(C)C[C@@H](OC1=O)[C@H]([C@@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H]2[C@]3([C@]1(C)C(=O)C=C[C@@H]3O)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047414
PubChem CID:	12147447
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

*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
NPO20281	Withania aristata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22705001]
NPO20281	Withania aristata	Species	Solanaceae	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	8
Others	1

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	17700.0	nM	PMID[482740]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[482740]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	19800.0	nM	PMID[482740]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	31700.0	nM	PMID[482740]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16300.0	nM	PMID[482740]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	10300.0	nM	PMID[482740]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	28800.0	nM	PMID[482740]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	21800.0	nM	PMID[482740]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Ratio IC50	=	1.8	n.a.	PMID[482740]

☑ 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 NPC264954 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	231
0.1-0.2	1319
0.2-0.3	3956
0.3-0.4	7818
0.4-0.5	12903
0.5-0.6	6831
0.6-0.7	6616
0.7-0.8	2698
0.8-0.85	217
0.85-0.9	52
0.9-0.95	44
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC474370
0.9817	High Similarity	NPC167606
0.9817	High Similarity	NPC286528
0.9817	High Similarity	NPC20302
0.9817	High Similarity	NPC140055
0.9817	High Similarity	NPC470492
0.9732	High Similarity	NPC88326
0.9732	High Similarity	NPC153700
0.9727	High Similarity	NPC50774
0.9727	High Similarity	NPC709
0.9636	High Similarity	NPC470493
0.9636	High Similarity	NPC312824
0.9636	High Similarity	NPC183580
0.9561	High Similarity	NPC8374
0.9541	High Similarity	NPC122056
0.9469	High Similarity	NPC470878
0.9469	High Similarity	NPC67569
0.9469	High Similarity	NPC473256
0.9455	High Similarity	NPC67259
0.9455	High Similarity	NPC147912
0.9386	High Similarity	NPC470265
0.9386	High Similarity	NPC23786
0.9375	High Similarity	NPC186525
0.9375	High Similarity	NPC329736
0.9304	High Similarity	NPC469789
0.9292	High Similarity	NPC473274
0.9292	High Similarity	NPC61520
0.9273	High Similarity	NPC191620
0.9224	High Similarity	NPC470494
0.9224	High Similarity	NPC3381
0.9224	High Similarity	NPC172154
0.9224	High Similarity	NPC8369
0.9224	High Similarity	NPC81736
0.9196	High Similarity	NPC270929
0.9145	High Similarity	NPC293112
0.9138	High Similarity	NPC11895
0.9123	High Similarity	NPC473270
0.9115	High Similarity	NPC243065
0.9052	High Similarity	NPC170538
0.9027	High Similarity	NPC64318
0.9009	High Similarity	NPC470961
0.9009	High Similarity	NPC474315
0.8966	High Similarity	NPC46570
0.8938	High Similarity	NPC284915
0.8919	High Similarity	NPC29133
0.8917	High Similarity	NPC473593
0.8889	High Similarity	NPC269642
0.8889	High Similarity	NPC107493
0.8824	High Similarity	NPC473635
0.8818	High Similarity	NPC91034
0.8814	High Similarity	NPC204812
0.8793	High Similarity	NPC475041
0.8783	High Similarity	NPC470959
0.8783	High Similarity	NPC476965
0.877	High Similarity	NPC231240
0.8761	High Similarity	NPC476163
0.875	High Similarity	NPC287423
0.875	High Similarity	NPC37116
0.875	High Similarity	NPC473253
0.8739	High Similarity	NPC241456
0.8739	High Similarity	NPC32868
0.8707	High Similarity	NPC311554
0.8707	High Similarity	NPC257457
0.8699	High Similarity	NPC316915
0.8661	High Similarity	NPC475065
0.8649	High Similarity	NPC330011
0.8649	High Similarity	NPC329048
0.8632	High Similarity	NPC476960
0.8632	High Similarity	NPC475520
0.8621	High Similarity	NPC471854
0.8607	High Similarity	NPC231529
0.8607	High Similarity	NPC470880
0.8596	High Similarity	NPC69291
0.8596	High Similarity	NPC236217
0.8595	High Similarity	NPC156797
0.8571	High Similarity	NPC475418
0.8571	High Similarity	NPC318363
0.8571	High Similarity	NPC472825
0.8571	High Similarity	NPC473482
0.8559	High Similarity	NPC79579
0.8559	High Similarity	NPC476961
0.8559	High Similarity	NPC268530
0.8559	High Similarity	NPC154491
0.8547	High Similarity	NPC153440
0.8537	High Similarity	NPC220757
0.8537	High Similarity	NPC196921
0.8534	High Similarity	NPC190286
0.8509	High Similarity	NPC470960
0.85	High Similarity	NPC120724
0.85	High Similarity	NPC473979
0.8496	Intermediate Similarity	NPC474901
0.8496	Intermediate Similarity	NPC475941
0.8487	Intermediate Similarity	NPC4021
0.8487	Intermediate Similarity	NPC159456
0.8482	Intermediate Similarity	NPC473284
0.8475	Intermediate Similarity	NPC5292
0.8475	Intermediate Similarity	NPC42673
0.8475	Intermediate Similarity	NPC473203
0.8462	Intermediate Similarity	NPC239273
0.8455	Intermediate Similarity	NPC476966
0.8455	Intermediate Similarity	NPC35109
0.8443	Intermediate Similarity	NPC470882
0.8443	Intermediate Similarity	NPC473265
0.8435	Intermediate Similarity	NPC475970
0.8435	Intermediate Similarity	NPC475524
0.8435	Intermediate Similarity	NPC100267
0.843	Intermediate Similarity	NPC469790
0.8421	Intermediate Similarity	NPC473627
0.8407	Intermediate Similarity	NPC220155
0.8403	Intermediate Similarity	NPC476962
0.8403	Intermediate Similarity	NPC251226
0.8403	Intermediate Similarity	NPC474585
0.84	Intermediate Similarity	NPC469673
0.839	Intermediate Similarity	NPC473720
0.8378	Intermediate Similarity	NPC475050
0.8376	Intermediate Similarity	NPC148458
0.8376	Intermediate Similarity	NPC176840
0.8376	Intermediate Similarity	NPC470075
0.8374	Intermediate Similarity	NPC473620
0.8364	Intermediate Similarity	NPC476897
0.8362	Intermediate Similarity	NPC317210
0.8362	Intermediate Similarity	NPC250109
0.8361	Intermediate Similarity	NPC159499
0.8347	Intermediate Similarity	NPC6193
0.8333	Intermediate Similarity	NPC476823
0.8333	Intermediate Similarity	NPC472216
0.8333	Intermediate Similarity	NPC214644
0.8333	Intermediate Similarity	NPC173905
0.8333	Intermediate Similarity	NPC5475
0.8333	Intermediate Similarity	NPC284828
0.832	Intermediate Similarity	NPC34963
0.8319	Intermediate Similarity	NPC305260
0.8319	Intermediate Similarity	NPC144459
0.8319	Intermediate Similarity	NPC270850
0.8319	Intermediate Similarity	NPC230513
0.8306	Intermediate Similarity	NPC471407
0.8305	Intermediate Similarity	NPC185287
0.8305	Intermediate Similarity	NPC55296
0.8305	Intermediate Similarity	NPC469684
0.8291	Intermediate Similarity	NPC474181
0.8276	Intermediate Similarity	NPC269530
0.8273	Intermediate Similarity	NPC474012
0.8273	Intermediate Similarity	NPC476299
0.8261	Intermediate Similarity	NPC76084
0.8261	Intermediate Similarity	NPC16270
0.8257	Intermediate Similarity	NPC253826
0.8254	Intermediate Similarity	NPC58029
0.8246	Intermediate Similarity	NPC177064
0.824	Intermediate Similarity	NPC173347
0.824	Intermediate Similarity	NPC241935
0.824	Intermediate Similarity	NPC279478
0.8235	Intermediate Similarity	NPC146786
0.8235	Intermediate Similarity	NPC475372
0.8235	Intermediate Similarity	NPC113448
0.823	Intermediate Similarity	NPC266570
0.823	Intermediate Similarity	NPC60681
0.8226	Intermediate Similarity	NPC311534
0.8214	Intermediate Similarity	NPC297617
0.8214	Intermediate Similarity	NPC112009
0.8214	Intermediate Similarity	NPC72151
0.8214	Intermediate Similarity	NPC329345
0.8214	Intermediate Similarity	NPC473283
0.8214	Intermediate Similarity	NPC476237
0.8214	Intermediate Similarity	NPC475526
0.8214	Intermediate Similarity	NPC26478
0.8211	Intermediate Similarity	NPC203702
0.8211	Intermediate Similarity	NPC15095
0.8211	Intermediate Similarity	NPC120994
0.8205	Intermediate Similarity	NPC962
0.8205	Intermediate Similarity	NPC25909
0.8198	Intermediate Similarity	NPC282524
0.819	Intermediate Similarity	NPC317107
0.819	Intermediate Similarity	NPC470076
0.8182	Intermediate Similarity	NPC316598
0.8182	Intermediate Similarity	NPC98868
0.8182	Intermediate Similarity	NPC470418
0.8182	Intermediate Similarity	NPC124512
0.8182	Intermediate Similarity	NPC310511
0.8182	Intermediate Similarity	NPC159763
0.8182	Intermediate Similarity	NPC478056
0.8182	Intermediate Similarity	NPC312481
0.8182	Intermediate Similarity	NPC278386
0.8175	Intermediate Similarity	NPC471855
0.8174	Intermediate Similarity	NPC87335
0.8174	Intermediate Similarity	NPC41405
0.8167	Intermediate Similarity	NPC312536
0.8167	Intermediate Similarity	NPC470495
0.8167	Intermediate Similarity	NPC278681
0.816	Intermediate Similarity	NPC221414
0.8158	Intermediate Similarity	NPC67321
0.8158	Intermediate Similarity	NPC131665
0.8158	Intermediate Similarity	NPC255387
0.8158	Intermediate Similarity	NPC475294
0.8158	Intermediate Similarity	NPC301666
0.8158	Intermediate Similarity	NPC79298
0.8158	Intermediate Similarity	NPC43063
0.8158	Intermediate Similarity	NPC187435
0.8151	Intermediate Similarity	NPC157380
0.8151	Intermediate Similarity	NPC284068
0.8151	Intermediate Similarity	NPC473656

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 NPC264954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	1466
0.2-0.3	3551
0.3-0.4	2579
0.4-0.5	817
0.5-0.6	241
0.6-0.7	156
0.7-0.8	134
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9817	High Similarity	NPD7115	Discovery
0.8182	Intermediate Similarity	NPD4225	Approved
0.812	Intermediate Similarity	NPD8297	Approved
0.8087	Intermediate Similarity	NPD6881	Approved
0.8087	Intermediate Similarity	NPD6899	Approved
0.8034	Intermediate Similarity	NPD6649	Approved
0.8034	Intermediate Similarity	NPD6650	Approved
0.8	Intermediate Similarity	NPD5697	Approved
0.7951	Intermediate Similarity	NPD6319	Approved
0.7949	Intermediate Similarity	NPD7290	Approved
0.7949	Intermediate Similarity	NPD7102	Approved
0.7949	Intermediate Similarity	NPD6883	Approved
0.7913	Intermediate Similarity	NPD6675	Approved
0.7913	Intermediate Similarity	NPD6402	Approved
0.7913	Intermediate Similarity	NPD7128	Approved
0.7913	Intermediate Similarity	NPD5739	Approved
0.7881	Intermediate Similarity	NPD6869	Approved
0.7881	Intermediate Similarity	NPD6617	Approved
0.7881	Intermediate Similarity	NPD6847	Approved
0.7881	Intermediate Similarity	NPD8130	Phase 1
0.7863	Intermediate Similarity	NPD6372	Approved
0.7863	Intermediate Similarity	NPD6012	Approved
0.7863	Intermediate Similarity	NPD6014	Approved
0.7863	Intermediate Similarity	NPD6013	Approved
0.7863	Intermediate Similarity	NPD6373	Approved
0.7815	Intermediate Similarity	NPD6882	Approved
0.7807	Intermediate Similarity	NPD5211	Phase 2
0.7788	Intermediate Similarity	NPD7640	Approved
0.7788	Intermediate Similarity	NPD7639	Approved
0.7778	Intermediate Similarity	NPD7320	Approved
0.7778	Intermediate Similarity	NPD6011	Approved
0.7768	Intermediate Similarity	NPD6083	Phase 2
0.7768	Intermediate Similarity	NPD6084	Phase 2
0.775	Intermediate Similarity	NPD4632	Approved
0.7734	Intermediate Similarity	NPD7319	Approved
0.7706	Intermediate Similarity	NPD5785	Approved
0.7699	Intermediate Similarity	NPD7638	Approved
0.7698	Intermediate Similarity	NPD7492	Approved
0.7692	Intermediate Similarity	NPD5701	Approved
0.7672	Intermediate Similarity	NPD5141	Approved
0.7661	Intermediate Similarity	NPD6054	Approved
0.7656	Intermediate Similarity	NPD7736	Approved
0.7647	Intermediate Similarity	NPD6371	Approved
0.7647	Intermediate Similarity	NPD4634	Approved
0.7638	Intermediate Similarity	NPD6616	Approved
0.7638	Intermediate Similarity	NPD7507	Approved
0.7632	Intermediate Similarity	NPD5286	Approved
0.7632	Intermediate Similarity	NPD4696	Approved
0.7632	Intermediate Similarity	NPD5285	Approved
0.7607	Intermediate Similarity	NPD6008	Approved
0.76	Intermediate Similarity	NPD7503	Approved
0.7589	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7078	Approved
0.7568	Intermediate Similarity	NPD6399	Phase 3
0.7563	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5696	Approved
0.754	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.748	Intermediate Similarity	NPD7604	Phase 2
0.7477	Intermediate Similarity	NPD6079	Approved
0.746	Intermediate Similarity	NPD6015	Approved
0.746	Intermediate Similarity	NPD6016	Approved
0.7456	Intermediate Similarity	NPD4755	Approved
0.744	Intermediate Similarity	NPD7101	Approved
0.744	Intermediate Similarity	NPD7100	Approved
0.7438	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5174	Approved
0.7436	Intermediate Similarity	NPD5175	Approved
0.7434	Intermediate Similarity	NPD4629	Approved
0.7434	Intermediate Similarity	NPD5695	Phase 3
0.7434	Intermediate Similarity	NPD5210	Approved
0.7419	Intermediate Similarity	NPD6009	Approved
0.7414	Intermediate Similarity	NPD5223	Approved
0.7411	Intermediate Similarity	NPD4202	Approved
0.7402	Intermediate Similarity	NPD5988	Approved
0.7395	Intermediate Similarity	NPD6412	Phase 2
0.7381	Intermediate Similarity	NPD6059	Approved
0.7364	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6335	Approved
0.736	Intermediate Similarity	NPD7328	Approved
0.736	Intermediate Similarity	NPD7327	Approved
0.7355	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7748	Approved
0.7339	Intermediate Similarity	NPD7521	Approved
0.7339	Intermediate Similarity	NPD7334	Approved
0.7339	Intermediate Similarity	NPD5330	Approved
0.7339	Intermediate Similarity	NPD7146	Approved
0.7339	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6409	Approved
0.7339	Intermediate Similarity	NPD3618	Phase 1
0.7339	Intermediate Similarity	NPD6274	Approved
0.7339	Intermediate Similarity	NPD6684	Approved
0.7328	Intermediate Similarity	NPD4700	Approved
0.7323	Intermediate Similarity	NPD5983	Phase 2
0.7323	Intermediate Similarity	NPD8033	Approved
0.7321	Intermediate Similarity	NPD7515	Phase 2
0.7321	Intermediate Similarity	NPD5693	Phase 1
0.7308	Intermediate Similarity	NPD8293	Discontinued
0.7304	Intermediate Similarity	NPD7902	Approved
0.7302	Intermediate Similarity	NPD7516	Approved
0.7297	Intermediate Similarity	NPD4753	Phase 2
0.7297	Intermediate Similarity	NPD5328	Approved
0.728	Intermediate Similarity	NPD6317	Approved
0.7248	Intermediate Similarity	NPD5363	Approved
0.7244	Intermediate Similarity	NPD8294	Approved
0.7244	Intermediate Similarity	NPD8377	Approved
0.7236	Intermediate Similarity	NPD6053	Discontinued
0.7231	Intermediate Similarity	NPD6336	Discontinued
0.7222	Intermediate Similarity	NPD6313	Approved
0.7222	Intermediate Similarity	NPD6314	Approved
0.7217	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5221	Approved
0.7217	Intermediate Similarity	NPD5222	Approved
0.7207	Intermediate Similarity	NPD6903	Approved
0.7203	Intermediate Similarity	NPD7632	Discontinued
0.7193	Intermediate Similarity	NPD6001	Approved
0.719	Intermediate Similarity	NPD6686	Approved
0.719	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4730	Approved
0.719	Intermediate Similarity	NPD4729	Approved
0.7188	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8379	Approved
0.7188	Intermediate Similarity	NPD8335	Approved
0.7188	Intermediate Similarity	NPD8378	Approved
0.7188	Intermediate Similarity	NPD8380	Approved
0.7188	Intermediate Similarity	NPD8296	Approved
0.7168	Intermediate Similarity	NPD5284	Approved
0.7168	Intermediate Similarity	NPD5281	Approved
0.7156	Intermediate Similarity	NPD3666	Approved
0.7156	Intermediate Similarity	NPD3133	Approved
0.7156	Intermediate Similarity	NPD4786	Approved
0.7156	Intermediate Similarity	NPD3665	Phase 1
0.7155	Intermediate Similarity	NPD5173	Approved
0.7143	Intermediate Similarity	NPD6673	Approved
0.7143	Intermediate Similarity	NPD6904	Approved
0.7143	Intermediate Similarity	NPD6080	Approved
0.7119	Intermediate Similarity	NPD5344	Discontinued
0.7107	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1694	Approved
0.7073	Intermediate Similarity	NPD5251	Approved
0.7073	Intermediate Similarity	NPD5250	Approved
0.7073	Intermediate Similarity	NPD5248	Approved
0.7073	Intermediate Similarity	NPD5249	Phase 3
0.7073	Intermediate Similarity	NPD5247	Approved
0.7069	Intermediate Similarity	NPD4697	Phase 3
0.7063	Intermediate Similarity	NPD6868	Approved
0.7054	Intermediate Similarity	NPD8513	Phase 3
0.7054	Intermediate Similarity	NPD6908	Approved
0.7054	Intermediate Similarity	NPD6909	Approved
0.7054	Intermediate Similarity	NPD6672	Approved
0.7054	Intermediate Similarity	NPD5737	Approved
0.7049	Intermediate Similarity	NPD5128	Approved
0.7043	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7900	Approved
0.7025	Intermediate Similarity	NPD4768	Approved
0.7025	Intermediate Similarity	NPD4767	Approved
0.7018	Intermediate Similarity	NPD8035	Phase 2
0.7018	Intermediate Similarity	NPD7637	Suspended
0.7018	Intermediate Similarity	NPD8034	Phase 2
0.7016	Intermediate Similarity	NPD5217	Approved
0.7016	Intermediate Similarity	NPD5216	Approved
0.7016	Intermediate Similarity	NPD5215	Approved
0.7	Intermediate Similarity	NPD4754	Approved
0.6991	Remote Similarity	NPD6051	Approved
0.6972	Remote Similarity	NPD4269	Approved
0.6972	Remote Similarity	NPD4223	Phase 3
0.6972	Remote Similarity	NPD4221	Approved
0.6972	Remote Similarity	NPD4270	Approved
0.6972	Remote Similarity	NPD3667	Approved
0.6967	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3573	Approved
0.6947	Remote Similarity	NPD8328	Phase 3
0.6937	Remote Similarity	NPD5329	Approved
0.6937	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5169	Approved
0.6935	Remote Similarity	NPD5135	Approved
0.6935	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD8516	Approved
0.6923	Remote Similarity	NPD8517	Approved
0.6923	Remote Similarity	NPD8515	Approved
0.6905	Remote Similarity	NPD8133	Approved
0.6903	Remote Similarity	NPD5208	Approved
0.6881	Remote Similarity	NPD5369	Approved
0.688	Remote Similarity	NPD5127	Approved
0.6875	Remote Similarity	NPD6098	Approved
0.6875	Remote Similarity	NPD5690	Phase 2
0.6875	Remote Similarity	NPD5786	Approved
0.687	Remote Similarity	NPD5694	Approved
0.687	Remote Similarity	NPD6411	Approved
0.687	Remote Similarity	NPD6050	Approved
0.6866	Remote Similarity	NPD6033	Approved
0.6847	Remote Similarity	NPD4197	Approved
0.6838	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4159	Approved
0.6818	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5778	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