NPASS Compound

Structure

NPC475834 OpenBabel07101718222D 35 40 0 0 1 0 0 0 0 0999 V2000 -4.1157 -1.7180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9291 0.1091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5334 -1.0135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5279 -0.9090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9346 0.0046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -2.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 -0.2045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3468 0.8136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -3.1180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -5.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7536 1.7271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 0.7091 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 15 1 0 0 0 0 2 16 1 0 0 0 0 5 33 1 0 0 0 0 6 7 1 0 0 0 0 7 20 2 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 2 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 16 25 1 0 0 0 0 17 6 1 1 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 27 1 6 0 0 0 19 29 1 6 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 21 30 1 6 0 0 0 22 28 1 6 0 0 0 22 29 1 0 0 0 0 23 27 1 0 0 0 0 23 31 2 0 0 0 0 24 14 1 1 0 0 0 24 28 1 0 0 0 0 24 34 1 0 0 0 0 25 32 2 0 0 0 0 25 34 1 0 0 0 0 26 29 1 6 0 0 0 26 33 1 0 0 0 0 26 35 1 0 0 0 0 27 3 1 6 0 0 0 28 4 1 1 0 0 0 28 35 1 0 0 0 0 29 13 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.27
Volume:	498.36
LogP:	3.185
LogD:	2.292
LogS:	-4.549
# Rotatable Bonds:	2
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	6.115
Fsp3:	0.759
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:	-4.804
MDCK Permeability:	1.6565803889534436e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.071
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.881

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978
Plasma Protein Binding (PPB):	53.24259567260742%
Volume Distribution (VD):	1.414
Pgp-substrate:	36.57745361328125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.694
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.348
CYP3A4-inhibitor:	0.769
CYP3A4-substrate:	0.378

ADMET: Excretion

Clearance (CL):	10.822
Half-life (T1/2):	0.578

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.773
Drug-inuced Liver Injury (DILI):	0.228
AMES Toxicity:	0.622
Rat Oral Acute Toxicity:	0.782
Maximum Recommended Daily Dose:	0.731
Skin Sensitization:	0.183
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC475834

Natural Product ID:	NPC475834
*Common Name:**	Withaphysalin I
IUPAC Name:	n.a.
Synonyms:	Withaphysalin I
Standard InCHIKey:	FKDPGSFHKKGFDE-UYFNPNMNSA-N
Standard InCHI:	InChI=1S/C29H38O6/c1-15-14-24(34-25(32)16(15)2)28(4)22-10-8-19-17-6-7-20-21(30)9-11-23(31)27(20,3)18(17)12-13-29(19,22)26(33-5)35-28/h7,9,11,17-19,21-22,24,26,30H,6,8,10,12-14H2,1-5H3/t17-,18+,19+,21+,22-,24-,26+,27-,28-,29-/m1/s1
SMILES:	CC1=C(C(=O)OC(C1)C2(C3CCC4C3(CCC5C4CC=C6C5(C(=O)C=CC6O)C)C(O2)OC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517041
PubChem CID:	21606683
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
NPO32672	vassobia lorentzii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO32672	vassobia lorentzii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21]
NPO32672	vassobia lorentzii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9]

☑ 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	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	1.04	uM	PMID[529977]
NPT2	Others	Unspecified		Ratio	=	5.1	n.a.	PMID[529977]
NPT27	Others	Unspecified		IC50	=	5270.0	nM	PMID[529977]

☑ 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 NPC475834 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	230
0.1-0.2	1272
0.2-0.3	4032
0.3-0.4	8486
0.4-0.5	12535
0.5-0.6	7130
0.6-0.7	6747
0.7-0.8	2168
0.8-0.85	81
0.85-0.9	6
0.9-0.95	3
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474179
0.9908	High Similarity	NPC475913
0.9279	High Similarity	NPC474181
0.9273	High Similarity	NPC236217
0.9076	High Similarity	NPC473593
0.875	High Similarity	NPC37116
0.8618	High Similarity	NPC231240
0.8607	High Similarity	NPC476966
0.8559	High Similarity	NPC474585
0.8548	High Similarity	NPC316915
0.8547	High Similarity	NPC291564
0.8537	High Similarity	NPC213634
0.8534	High Similarity	NPC190286
0.8534	High Similarity	NPC176840
0.8525	High Similarity	NPC473620
0.8525	High Similarity	NPC245094
0.8487	Intermediate Similarity	NPC202051
0.8487	Intermediate Similarity	NPC67569
0.8487	Intermediate Similarity	NPC46570
0.8487	Intermediate Similarity	NPC470418
0.8482	Intermediate Similarity	NPC91034
0.8475	Intermediate Similarity	NPC477071
0.8455	Intermediate Similarity	NPC471407
0.8448	Intermediate Similarity	NPC471398
0.8443	Intermediate Similarity	NPC42399
0.8435	Intermediate Similarity	NPC191620
0.843	Intermediate Similarity	NPC8369
0.843	Intermediate Similarity	NPC318135
0.8421	Intermediate Similarity	NPC473627
0.8421	Intermediate Similarity	NPC235014
0.8421	Intermediate Similarity	NPC29133
0.8417	Intermediate Similarity	NPC470265
0.8417	Intermediate Similarity	NPC23786
0.8417	Intermediate Similarity	NPC107493
0.8403	Intermediate Similarity	NPC79579
0.839	Intermediate Similarity	NPC153440
0.8362	Intermediate Similarity	NPC157441
0.8348	Intermediate Similarity	NPC470961
0.8347	Intermediate Similarity	NPC469789
0.8347	Intermediate Similarity	NPC41129
0.8333	Intermediate Similarity	NPC129434
0.832	Intermediate Similarity	NPC471855
0.8319	Intermediate Similarity	NPC473274
0.8319	Intermediate Similarity	NPC5292
0.8319	Intermediate Similarity	NPC475041
0.8319	Intermediate Similarity	NPC232258
0.8305	Intermediate Similarity	NPC23046
0.8304	Intermediate Similarity	NPC100955
0.8304	Intermediate Similarity	NPC121566
0.8293	Intermediate Similarity	NPC152091
0.8291	Intermediate Similarity	NPC220293
0.8288	Intermediate Similarity	NPC134077
0.8288	Intermediate Similarity	NPC475320
0.8279	Intermediate Similarity	NPC3381
0.8276	Intermediate Similarity	NPC194951
0.8276	Intermediate Similarity	NPC12046
0.8264	Intermediate Similarity	NPC473231
0.8264	Intermediate Similarity	NPC470419
0.825	Intermediate Similarity	NPC470312
0.825	Intermediate Similarity	NPC48692
0.8235	Intermediate Similarity	NPC45475
0.8235	Intermediate Similarity	NPC50774
0.8235	Intermediate Similarity	NPC709
0.823	Intermediate Similarity	NPC95243
0.823	Intermediate Similarity	NPC63023
0.823	Intermediate Similarity	NPC96377
0.823	Intermediate Similarity	NPC162033
0.8226	Intermediate Similarity	NPC473888
0.8226	Intermediate Similarity	NPC311534
0.8211	Intermediate Similarity	NPC293112
0.8205	Intermediate Similarity	NPC293658
0.8205	Intermediate Similarity	NPC474410
0.8205	Intermediate Similarity	NPC25909
0.8198	Intermediate Similarity	NPC63249
0.8182	Intermediate Similarity	NPC473256
0.8182	Intermediate Similarity	NPC204731
0.8182	Intermediate Similarity	NPC473250
0.8182	Intermediate Similarity	NPC470878
0.8174	Intermediate Similarity	NPC246205
0.8167	Intermediate Similarity	NPC305260
0.8167	Intermediate Similarity	NPC161065
0.8167	Intermediate Similarity	NPC270850
0.8167	Intermediate Similarity	NPC473270
0.816	Intermediate Similarity	NPC104382
0.8151	Intermediate Similarity	NPC20302
0.8151	Intermediate Similarity	NPC167606
0.8151	Intermediate Similarity	NPC286528
0.8151	Intermediate Similarity	NPC140055
0.8151	Intermediate Similarity	NPC473656
0.8145	Intermediate Similarity	NPC287423
0.8145	Intermediate Similarity	NPC298841
0.8142	Intermediate Similarity	NPC255309
0.8142	Intermediate Similarity	NPC223741
0.8136	Intermediate Similarity	NPC147912
0.8136	Intermediate Similarity	NPC67259
0.813	Intermediate Similarity	NPC8374
0.8115	Intermediate Similarity	NPC287236
0.8115	Intermediate Similarity	NPC269642
0.8103	Intermediate Similarity	NPC101450
0.8103	Intermediate Similarity	NPC27551
0.8103	Intermediate Similarity	NPC5103
0.8103	Intermediate Similarity	NPC114961
0.8099	Intermediate Similarity	NPC241192
0.8099	Intermediate Similarity	NPC474370
0.8095	Intermediate Similarity	NPC173347
0.8087	Intermediate Similarity	NPC295389
0.8087	Intermediate Similarity	NPC392
0.8087	Intermediate Similarity	NPC219900
0.8087	Intermediate Similarity	NPC177524
0.8087	Intermediate Similarity	NPC220155
0.8083	Intermediate Similarity	NPC186525
0.8083	Intermediate Similarity	NPC234522
0.8083	Intermediate Similarity	NPC473617
0.8083	Intermediate Similarity	NPC473828
0.808	Intermediate Similarity	NPC470850
0.807	Intermediate Similarity	NPC127790
0.807	Intermediate Similarity	NPC470309
0.807	Intermediate Similarity	NPC127609
0.8067	Intermediate Similarity	NPC302471
0.8067	Intermediate Similarity	NPC268213
0.8067	Intermediate Similarity	NPC64318
0.8067	Intermediate Similarity	NPC207637
0.8065	Intermediate Similarity	NPC93368
0.8053	Intermediate Similarity	NPC36688
0.8051	Intermediate Similarity	NPC477944
0.8051	Intermediate Similarity	NPC469496
0.8051	Intermediate Similarity	NPC73455
0.8051	Intermediate Similarity	NPC471627
0.8051	Intermediate Similarity	NPC122056
0.8051	Intermediate Similarity	NPC469454
0.8051	Intermediate Similarity	NPC469463
0.8051	Intermediate Similarity	NPC471173
0.8051	Intermediate Similarity	NPC200944
0.8049	Intermediate Similarity	NPC27363
0.8049	Intermediate Similarity	NPC11895
0.8049	Intermediate Similarity	NPC473979
0.8034	Intermediate Similarity	NPC474315
0.8034	Intermediate Similarity	NPC324683
0.8033	Intermediate Similarity	NPC476204
0.8033	Intermediate Similarity	NPC170084
0.8031	Intermediate Similarity	NPC155529
0.8017	Intermediate Similarity	NPC112457
0.8017	Intermediate Similarity	NPC475520
0.8017	Intermediate Similarity	NPC264954
0.8016	Intermediate Similarity	NPC175186
0.8	Intermediate Similarity	NPC470493
0.8	Intermediate Similarity	NPC470492
0.8	Intermediate Similarity	NPC312824
0.8	Intermediate Similarity	NPC203862
0.8	Intermediate Similarity	NPC183580
0.8	Intermediate Similarity	NPC473968
0.8	Intermediate Similarity	NPC284068
0.7984	Intermediate Similarity	NPC81736
0.7984	Intermediate Similarity	NPC241456
0.7984	Intermediate Similarity	NPC172154
0.7984	Intermediate Similarity	NPC32868
0.7984	Intermediate Similarity	NPC158350
0.7983	Intermediate Similarity	NPC74727
0.7983	Intermediate Similarity	NPC473882
0.7983	Intermediate Similarity	NPC475163
0.7982	Intermediate Similarity	NPC146731
0.7982	Intermediate Similarity	NPC222161
0.7982	Intermediate Similarity	NPC296950
0.7967	Intermediate Similarity	NPC153700
0.7967	Intermediate Similarity	NPC170538
0.7967	Intermediate Similarity	NPC28532
0.7967	Intermediate Similarity	NPC88326
0.7965	Intermediate Similarity	NPC469606
0.7965	Intermediate Similarity	NPC273005
0.7965	Intermediate Similarity	NPC31058
0.7965	Intermediate Similarity	NPC235369
0.7965	Intermediate Similarity	NPC137430
0.7953	Intermediate Similarity	NPC471170
0.7951	Intermediate Similarity	NPC281840
0.7949	Intermediate Similarity	NPC154856
0.7949	Intermediate Similarity	NPC129340
0.7949	Intermediate Similarity	NPC475317
0.7949	Intermediate Similarity	NPC52241
0.7949	Intermediate Similarity	NPC163314
0.7946	Intermediate Similarity	NPC241221
0.7937	Intermediate Similarity	NPC45606
0.7937	Intermediate Similarity	NPC220838
0.7934	Intermediate Similarity	NPC475372
0.7931	Intermediate Similarity	NPC189075
0.7931	Intermediate Similarity	NPC469844
0.7931	Intermediate Similarity	NPC325054
0.7931	Intermediate Similarity	NPC275539
0.7928	Intermediate Similarity	NPC257726
0.7928	Intermediate Similarity	NPC204054
0.7928	Intermediate Similarity	NPC98112
0.7928	Intermediate Similarity	NPC476253
0.7923	Intermediate Similarity	NPC245017
0.792	Intermediate Similarity	NPC469750
0.792	Intermediate Similarity	NPC250556
0.792	Intermediate Similarity	NPC174367
0.792	Intermediate Similarity	NPC47113
0.792	Intermediate Similarity	NPC473635
0.7917	Intermediate Similarity	NPC113425
0.7917	Intermediate Similarity	NPC49492
0.7917	Intermediate Similarity	NPC148458

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 NPC475834 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1465
0.2-0.3	3712
0.3-0.4	2517
0.4-0.5	743
0.5-0.6	253
0.6-0.7	218
0.7-0.8	42
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8151	Intermediate Similarity	NPD7115	Discovery
0.8087	Intermediate Similarity	NPD6686	Approved
0.8	Intermediate Similarity	NPD6412	Phase 2
0.7937	Intermediate Similarity	NPD7736	Approved
0.792	Intermediate Similarity	NPD7507	Approved
0.7886	Intermediate Similarity	NPD7503	Approved
0.7823	Intermediate Similarity	NPD6370	Approved
0.7734	Intermediate Similarity	NPD7319	Approved
0.7698	Intermediate Similarity	NPD7492	Approved
0.7661	Intermediate Similarity	NPD6054	Approved
0.7642	Intermediate Similarity	NPD7327	Approved
0.7642	Intermediate Similarity	NPD7328	Approved
0.7638	Intermediate Similarity	NPD6616	Approved
0.76	Intermediate Similarity	NPD8033	Approved
0.7581	Intermediate Similarity	NPD7516	Approved
0.7578	Intermediate Similarity	NPD7078	Approved
0.7578	Intermediate Similarity	NPD8293	Discontinued
0.7561	Intermediate Similarity	NPD6009	Approved
0.7521	Intermediate Similarity	NPD6053	Discontinued
0.752	Intermediate Similarity	NPD8377	Approved
0.752	Intermediate Similarity	NPD8294	Approved
0.7478	Intermediate Similarity	NPD7640	Approved
0.7478	Intermediate Similarity	NPD7639	Approved
0.746	Intermediate Similarity	NPD8380	Approved
0.746	Intermediate Similarity	NPD8378	Approved
0.746	Intermediate Similarity	NPD8379	Approved
0.746	Intermediate Similarity	NPD6015	Approved
0.746	Intermediate Similarity	NPD6016	Approved
0.746	Intermediate Similarity	NPD8513	Phase 3
0.746	Intermediate Similarity	NPD8335	Approved
0.746	Intermediate Similarity	NPD8296	Approved
0.7438	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD6399	Phase 3
0.7402	Intermediate Similarity	NPD5988	Approved
0.7391	Intermediate Similarity	NPD7638	Approved
0.7381	Intermediate Similarity	NPD6059	Approved
0.7377	Intermediate Similarity	NPD6882	Approved
0.7323	Intermediate Similarity	NPD8516	Approved
0.7323	Intermediate Similarity	NPD8517	Approved
0.7323	Intermediate Similarity	NPD8515	Approved
0.7317	Intermediate Similarity	NPD8133	Approved
0.7317	Intermediate Similarity	NPD4632	Approved
0.7311	Intermediate Similarity	NPD6008	Approved
0.7273	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD8297	Approved
0.7213	Intermediate Similarity	NPD6371	Approved
0.7209	Intermediate Similarity	NPD6067	Discontinued
0.719	Intermediate Similarity	NPD6881	Approved
0.719	Intermediate Similarity	NPD6899	Approved
0.7168	Intermediate Similarity	NPD5284	Approved
0.7168	Intermediate Similarity	NPD5281	Approved
0.7155	Intermediate Similarity	NPD6083	Phase 2
0.7155	Intermediate Similarity	NPD6084	Phase 2
0.7154	Intermediate Similarity	NPD6650	Approved
0.7154	Intermediate Similarity	NPD6649	Approved
0.713	Intermediate Similarity	NPD5695	Phase 3
0.7109	Intermediate Similarity	NPD6319	Approved
0.7107	Intermediate Similarity	NPD5697	Approved
0.7094	Intermediate Similarity	NPD4225	Approved
0.709	Intermediate Similarity	NPD7260	Phase 2
0.708	Intermediate Similarity	NPD5207	Approved
0.708	Intermediate Similarity	NPD5785	Approved
0.7077	Intermediate Similarity	NPD8328	Phase 3
0.7077	Intermediate Similarity	NPD7604	Phase 2
0.7073	Intermediate Similarity	NPD6883	Approved
0.7073	Intermediate Similarity	NPD7290	Approved
0.7073	Intermediate Similarity	NPD7102	Approved
0.7054	Intermediate Similarity	NPD5983	Phase 2
0.7049	Intermediate Similarity	NPD6011	Approved
0.7049	Intermediate Similarity	NPD7320	Approved
0.7025	Intermediate Similarity	NPD7128	Approved
0.7025	Intermediate Similarity	NPD5739	Approved
0.7025	Intermediate Similarity	NPD6675	Approved
0.7025	Intermediate Similarity	NPD6402	Approved
0.7016	Intermediate Similarity	NPD8130	Phase 1
0.7016	Intermediate Similarity	NPD6847	Approved
0.7016	Intermediate Similarity	NPD6617	Approved
0.7016	Intermediate Similarity	NPD6869	Approved
0.7015	Intermediate Similarity	NPD5956	Approved
0.6992	Remote Similarity	NPD6014	Approved
0.6992	Remote Similarity	NPD6033	Approved
0.6992	Remote Similarity	NPD6013	Approved
0.6992	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6372	Approved
0.6992	Remote Similarity	NPD6373	Approved
0.6992	Remote Similarity	NPD6012	Approved
0.6983	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6336	Discontinued
0.6967	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5696	Approved
0.6937	Remote Similarity	NPD1694	Approved
0.6935	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7632	Discontinued
0.6917	Remote Similarity	NPD5211	Phase 2
0.6912	Remote Similarity	NPD6845	Suspended
0.6903	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5737	Approved
0.6903	Remote Similarity	NPD6903	Approved
0.6903	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD5330	Approved
0.6875	Remote Similarity	NPD6684	Approved
0.6875	Remote Similarity	NPD7334	Approved
0.6875	Remote Similarity	NPD6409	Approved
0.6875	Remote Similarity	NPD7146	Approved
0.6875	Remote Similarity	NPD7521	Approved
0.687	Remote Similarity	NPD5693	Phase 1
0.687	Remote Similarity	NPD6079	Approved
0.6864	Remote Similarity	NPD7902	Approved
0.6847	Remote Similarity	NPD4786	Approved
0.6847	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4629	Approved
0.6838	Remote Similarity	NPD5210	Approved
0.6829	Remote Similarity	NPD5701	Approved
0.6803	Remote Similarity	NPD5141	Approved
0.6794	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD46	Approved
0.6783	Remote Similarity	NPD6698	Approved
0.6752	Remote Similarity	NPD7748	Approved
0.675	Remote Similarity	NPD5285	Approved
0.675	Remote Similarity	NPD5286	Approved
0.675	Remote Similarity	NPD4696	Approved
0.6746	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5690	Phase 2
0.6726	Remote Similarity	NPD5279	Phase 3
0.6726	Remote Similarity	NPD3618	Phase 1
0.6724	Remote Similarity	NPD6050	Approved
0.6724	Remote Similarity	NPD7515	Phase 2
0.6724	Remote Similarity	NPD7637	Suspended
0.6724	Remote Similarity	NPD5694	Approved
0.6696	Remote Similarity	NPD3665	Phase 1
0.6696	Remote Similarity	NPD5328	Approved
0.6696	Remote Similarity	NPD6080	Approved
0.6696	Remote Similarity	NPD6673	Approved
0.6696	Remote Similarity	NPD3133	Approved
0.6696	Remote Similarity	NPD6904	Approved
0.6696	Remote Similarity	NPD3666	Approved
0.6696	Remote Similarity	NPD4753	Phase 2
0.6694	Remote Similarity	NPD5223	Approved
0.6694	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5344	Discontinued
0.6692	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD5779	Approved
0.6641	Remote Similarity	NPD7101	Approved
0.6641	Remote Similarity	NPD7100	Approved
0.664	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5221	Approved
0.6639	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4633	Approved
0.6639	Remote Similarity	NPD5222	Approved
0.6639	Remote Similarity	NPD5226	Approved
0.6639	Remote Similarity	NPD5224	Approved
0.6639	Remote Similarity	NPD5225	Approved
0.6638	Remote Similarity	NPD5692	Phase 3
0.6637	Remote Similarity	NPD5363	Approved
0.6615	Remote Similarity	NPD6317	Approved
0.661	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7900	Approved
0.661	Remote Similarity	NPD6001	Approved
0.661	Remote Similarity	NPD5282	Discontinued
0.6607	Remote Similarity	NPD5362	Discontinued
0.6606	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5174	Approved
0.6585	Remote Similarity	NPD5175	Approved
0.6583	Remote Similarity	NPD5173	Approved
0.6583	Remote Similarity	NPD4755	Approved
0.6581	Remote Similarity	NPD8035	Phase 2
0.6581	Remote Similarity	NPD8034	Phase 2
0.6565	Remote Similarity	NPD6313	Approved
0.6565	Remote Similarity	NPD6314	Approved
0.6552	Remote Similarity	NPD1695	Approved
0.6552	Remote Similarity	NPD6051	Approved
0.6538	Remote Similarity	NPD6868	Approved
0.6538	Remote Similarity	NPD6274	Approved
0.6522	Remote Similarity	NPD7799	Discontinued
0.6522	Remote Similarity	NPD4250	Approved
0.6522	Remote Similarity	NPD4251	Approved
0.6518	Remote Similarity	NPD4221	Approved
0.6518	Remote Similarity	NPD4223	Phase 3
0.65	Remote Similarity	NPD4697	Phase 3
0.6496	Remote Similarity	NPD8337	Approved
0.6496	Remote Similarity	NPD7838	Discovery
0.6496	Remote Similarity	NPD8336	Approved
0.6491	Remote Similarity	NPD5329	Approved
0.6475	Remote Similarity	NPD6648	Approved
0.6475	Remote Similarity	NPD4700	Approved
0.6475	Remote Similarity	NPD6404	Discontinued
0.6466	Remote Similarity	NPD5208	Approved
0.6452	Remote Similarity	NPD6052	Approved
0.6441	Remote Similarity	NPD6411	Approved
0.6435	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6098	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