NPASS Compound

Structure

NPC474181 OpenBabel07101719252D 34 39 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 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 0 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 14 1 0 0 0 0 2 15 1 0 0 0 0 5 6 1 0 0 0 0 6 19 2 0 0 0 0 7 9 1 0 0 0 0 7 18 1 0 0 0 0 8 10 2 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 15 24 1 0 0 0 0 16 5 1 1 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 26 1 6 0 0 0 18 28 1 6 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 29 1 6 0 0 0 21 27 1 6 0 0 0 21 28 1 0 0 0 0 22 26 1 0 0 0 0 22 30 2 0 0 0 0 23 13 1 1 0 0 0 23 27 1 0 0 0 0 23 33 1 0 0 0 0 24 31 2 0 0 0 0 24 33 1 0 0 0 0 25 28 1 0 0 0 0 25 32 2 0 0 0 0 25 34 1 0 0 0 0 26 3 1 6 0 0 0 27 4 1 1 0 0 0 27 34 1 0 0 0 0 28 12 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.24
Volume:	478.428
LogP:	2.653
LogD:	1.916
LogS:	-4.534
# Rotatable Bonds:	1
TPSA:	86.74
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	5.868
Fsp3:	0.714
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:	-4.897
MDCK Permeability:	2.040682011283934e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.047
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.827
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.962
Plasma Protein Binding (PPB):	70.0362777709961%
Volume Distribution (VD):	0.698
Pgp-substrate:	20.27322006225586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.381
CYP2C19-inhibitor:	0.625
CYP2C19-substrate:	0.562
CYP2C9-inhibitor:	0.508
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.611
CYP3A4-inhibitor:	0.867
CYP3A4-substrate:	0.449

ADMET: Excretion

Clearance (CL):	12.094
Half-life (T1/2):	0.731

ADMET: Toxicity

hERG Blockers:	0.185
Human Hepatotoxicity (H-HT):	0.923
Drug-inuced Liver Injury (DILI):	0.192
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.435
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.279
Carcinogencity:	0.261
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.228

Download Data

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

Natural Product: NPC474181

Natural Product ID:	NPC474181
*Common Name:**	Withaphysalin J
IUPAC Name:	n.a.
Synonyms:	Withaphysalin J
Standard InCHIKey:	KUMLKGYHDQWUCK-NLKZUSOOSA-N
Standard InCHI:	InChI=1S/C28H34O6/c1-14-13-23(33-24(31)15(14)2)27(4)21-9-7-18-16-5-6-19-20(29)8-10-22(30)26(19,3)17(16)11-12-28(18,21)25(32)34-27/h6,8,10,16-18,20-21,23,29H,5,7,9,11-13H2,1-4H3/t16-,17+,18+,20+,21-,23-,26-,27-,28-/m1/s1
SMILES:	CC1=C(C)C(=O)O[C@H](C1)[C@]1(C)OC(=O)[C@]23[C@@H]1CC[C@H]3[C@H]1[C@H](CC2)[C@@]2(C)C(=O)C=C[C@@H](C2=CC1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463251
PubChem CID:	21606684
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	=	0.39	uM	PMID[533629]
NPT2	Others	Unspecified		Ratio	=	28.1	n.a.	PMID[533629]
NPT27	Others	Unspecified		IC50	=	11000.0	nM	PMID[533629]

☑ 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 NPC474181 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	217
0.1-0.2	1173
0.2-0.3	3873
0.3-0.4	7880
0.4-0.5	13143
0.5-0.6	7231
0.6-0.7	6828
0.7-0.8	2151
0.8-0.85	162
0.85-0.9	25
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9439	High Similarity	NPC236217
0.9434	High Similarity	NPC37116
0.9364	High Similarity	NPC475913
0.9279	High Similarity	NPC475834
0.9279	High Similarity	NPC474179
0.9074	High Similarity	NPC473627
0.9043	High Similarity	NPC8369
0.9027	High Similarity	NPC474585
0.9009	High Similarity	NPC176840
0.9009	High Similarity	NPC190286
0.8947	High Similarity	NPC46570
0.8879	High Similarity	NPC96377
0.887	High Similarity	NPC107493
0.886	High Similarity	NPC79579
0.885	High Similarity	NPC153440
0.8796	High Similarity	NPC91034
0.8793	High Similarity	NPC469789
0.8785	High Similarity	NPC255309
0.8772	High Similarity	NPC475041
0.8772	High Similarity	NPC5292
0.8739	High Similarity	NPC191620
0.8727	High Similarity	NPC29133
0.8661	High Similarity	NPC25909
0.8649	High Similarity	NPC470961
0.8644	High Similarity	NPC293112
0.8632	High Similarity	NPC11895
0.8621	High Similarity	NPC67569
0.8609	High Similarity	NPC270850
0.8609	High Similarity	NPC475520
0.8609	High Similarity	NPC305260
0.8598	High Similarity	NPC475320
0.8596	High Similarity	NPC284068
0.8559	High Similarity	NPC5103
0.8559	High Similarity	NPC81736
0.8559	High Similarity	NPC172154
0.8547	High Similarity	NPC470265
0.8547	High Similarity	NPC269642
0.8547	High Similarity	NPC170538
0.8547	High Similarity	NPC23786
0.8509	High Similarity	NPC148458
0.8496	Intermediate Similarity	NPC469463
0.8496	Intermediate Similarity	NPC469454
0.8496	Intermediate Similarity	NPC469496
0.8491	Intermediate Similarity	NPC23364
0.8475	Intermediate Similarity	NPC473979
0.8475	Intermediate Similarity	NPC120724
0.8455	Intermediate Similarity	NPC475294
0.8448	Intermediate Similarity	NPC230513
0.8435	Intermediate Similarity	NPC286528
0.8435	Intermediate Similarity	NPC20302
0.8435	Intermediate Similarity	NPC140055
0.8435	Intermediate Similarity	NPC167606
0.843	Intermediate Similarity	NPC473593
0.8426	Intermediate Similarity	NPC235369
0.8421	Intermediate Similarity	NPC67259
0.8421	Intermediate Similarity	NPC470953
0.8421	Intermediate Similarity	NPC147912
0.8421	Intermediate Similarity	NPC471398
0.8407	Intermediate Similarity	NPC221144
0.8378	Intermediate Similarity	NPC220155
0.8378	Intermediate Similarity	NPC189075
0.8378	Intermediate Similarity	NPC275539
0.8376	Intermediate Similarity	NPC476961
0.8376	Intermediate Similarity	NPC476962
0.8362	Intermediate Similarity	NPC709
0.8362	Intermediate Similarity	NPC50774
0.8362	Intermediate Similarity	NPC473720
0.8349	Intermediate Similarity	NPC474775
0.8349	Intermediate Similarity	NPC36688
0.8348	Intermediate Similarity	NPC266728
0.8348	Intermediate Similarity	NPC49492
0.8347	Intermediate Similarity	NPC473620
0.8333	Intermediate Similarity	NPC472924
0.8333	Intermediate Similarity	NPC310981
0.8333	Intermediate Similarity	NPC473635
0.8333	Intermediate Similarity	NPC224720
0.8333	Intermediate Similarity	NPC476240
0.8333	Intermediate Similarity	NPC122056
0.8333	Intermediate Similarity	NPC476223
0.8319	Intermediate Similarity	NPC474315
0.8319	Intermediate Similarity	NPC324683
0.8319	Intermediate Similarity	NPC304180
0.8319	Intermediate Similarity	NPC179798
0.8318	Intermediate Similarity	NPC197386
0.8302	Intermediate Similarity	NPC328371
0.8291	Intermediate Similarity	NPC476960
0.8291	Intermediate Similarity	NPC264954
0.8291	Intermediate Similarity	NPC42673
0.8288	Intermediate Similarity	NPC110496
0.8288	Intermediate Similarity	NPC473037
0.8279	Intermediate Similarity	NPC231529
0.8276	Intermediate Similarity	NPC469684
0.8276	Intermediate Similarity	NPC473656
0.8276	Intermediate Similarity	NPC470493
0.8276	Intermediate Similarity	NPC312824
0.8276	Intermediate Similarity	NPC183580
0.8276	Intermediate Similarity	NPC239273
0.8276	Intermediate Similarity	NPC470492
0.8273	Intermediate Similarity	NPC228669
0.8273	Intermediate Similarity	NPC164835
0.8264	Intermediate Similarity	NPC287423
0.825	Intermediate Similarity	NPC8374
0.8246	Intermediate Similarity	NPC100267
0.8246	Intermediate Similarity	NPC475524
0.8246	Intermediate Similarity	NPC126691
0.8246	Intermediate Similarity	NPC269530
0.8241	Intermediate Similarity	NPC241221
0.8241	Intermediate Similarity	NPC287833
0.8241	Intermediate Similarity	NPC476274
0.8235	Intermediate Similarity	NPC470419
0.823	Intermediate Similarity	NPC473036
0.823	Intermediate Similarity	NPC197428
0.823	Intermediate Similarity	NPC5284
0.823	Intermediate Similarity	NPC272898
0.822	Intermediate Similarity	NPC474370
0.8211	Intermediate Similarity	NPC213634
0.8208	Intermediate Similarity	NPC318282
0.8208	Intermediate Similarity	NPC174948
0.8208	Intermediate Similarity	NPC469995
0.8208	Intermediate Similarity	NPC281134
0.8208	Intermediate Similarity	NPC173875
0.8205	Intermediate Similarity	NPC186525
0.8198	Intermediate Similarity	NPC127609
0.8198	Intermediate Similarity	NPC323834
0.8198	Intermediate Similarity	NPC469607
0.8197	Intermediate Similarity	NPC473888
0.8197	Intermediate Similarity	NPC245094
0.819	Intermediate Similarity	NPC270929
0.819	Intermediate Similarity	NPC476963
0.819	Intermediate Similarity	NPC64318
0.8182	Intermediate Similarity	NPC236390
0.8174	Intermediate Similarity	NPC472926
0.8174	Intermediate Similarity	NPC56448
0.8174	Intermediate Similarity	NPC250109
0.8174	Intermediate Similarity	NPC962
0.8167	Intermediate Similarity	NPC204812
0.8158	Intermediate Similarity	NPC188738
0.8151	Intermediate Similarity	NPC202051
0.8151	Intermediate Similarity	NPC470418
0.8148	Intermediate Similarity	NPC98868
0.8142	Intermediate Similarity	NPC304495
0.8136	Intermediate Similarity	NPC472933
0.8131	Intermediate Similarity	NPC58052
0.8131	Intermediate Similarity	NPC111684
0.8125	Intermediate Similarity	NPC59530
0.8125	Intermediate Similarity	NPC472925
0.812	Intermediate Similarity	NPC470959
0.812	Intermediate Similarity	NPC472927
0.812	Intermediate Similarity	NPC472934
0.812	Intermediate Similarity	NPC23046
0.812	Intermediate Similarity	NPC476965
0.812	Intermediate Similarity	NPC476959
0.812	Intermediate Similarity	NPC473968
0.8115	Intermediate Similarity	NPC42399
0.8115	Intermediate Similarity	NPC473265
0.8115	Intermediate Similarity	NPC473253
0.8115	Intermediate Similarity	NPC470882
0.8113	Intermediate Similarity	NPC184870
0.8108	Intermediate Similarity	NPC471293
0.8108	Intermediate Similarity	NPC296950
0.8108	Intermediate Similarity	NPC146731
0.8108	Intermediate Similarity	NPC258532
0.8103	Intermediate Similarity	NPC326542
0.8099	Intermediate Similarity	NPC318135
0.8099	Intermediate Similarity	NPC32868
0.8099	Intermediate Similarity	NPC241456
0.8091	Intermediate Similarity	NPC136289
0.8091	Intermediate Similarity	NPC469606
0.8091	Intermediate Similarity	NPC195290
0.8091	Intermediate Similarity	NPC293753
0.8091	Intermediate Similarity	NPC137430
0.8091	Intermediate Similarity	NPC273005
0.8091	Intermediate Similarity	NPC119601
0.8091	Intermediate Similarity	NPC31058
0.8091	Intermediate Similarity	NPC204450
0.8091	Intermediate Similarity	NPC308726
0.8087	Intermediate Similarity	NPC207251
0.8087	Intermediate Similarity	NPC12046
0.8087	Intermediate Similarity	NPC470063
0.8087	Intermediate Similarity	NPC194951
0.8083	Intermediate Similarity	NPC88326
0.8083	Intermediate Similarity	NPC153700
0.8083	Intermediate Similarity	NPC222688
0.8073	Intermediate Similarity	NPC218383
0.8073	Intermediate Similarity	NPC51370
0.807	Intermediate Similarity	NPC286880
0.8067	Intermediate Similarity	NPC109973
0.8067	Intermediate Similarity	NPC268530
0.8067	Intermediate Similarity	NPC154491
0.8056	Intermediate Similarity	NPC320306
0.8056	Intermediate Similarity	NPC475894
0.8056	Intermediate Similarity	NPC121339
0.8056	Intermediate Similarity	NPC474343
0.8053	Intermediate Similarity	NPC472825
0.8051	Intermediate Similarity	NPC257457
0.8051	Intermediate Similarity	NPC329736
0.8051	Intermediate Similarity	NPC311554
0.8051	Intermediate Similarity	NPC475372
0.8037	Intermediate Similarity	NPC171395
0.8034	Intermediate Similarity	NPC196931

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 NPC474181 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1361
0.2-0.3	3694
0.3-0.4	2557
0.4-0.5	818
0.5-0.6	253
0.6-0.7	207
0.7-0.8	72
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8435	Intermediate Similarity	NPD7115	Discovery
0.7931	Intermediate Similarity	NPD6053	Discontinued
0.7748	Intermediate Similarity	NPD7640	Approved
0.7748	Intermediate Similarity	NPD7639	Approved
0.7719	Intermediate Similarity	NPD6008	Approved
0.7712	Intermediate Similarity	NPD4632	Approved
0.7661	Intermediate Similarity	NPD7492	Approved
0.7658	Intermediate Similarity	NPD7638	Approved
0.7627	Intermediate Similarity	NPD8297	Approved
0.7623	Intermediate Similarity	NPD6054	Approved
0.7619	Intermediate Similarity	NPD7736	Approved
0.76	Intermediate Similarity	NPD6616	Approved
0.76	Intermediate Similarity	NPD7507	Approved
0.7586	Intermediate Similarity	NPD6899	Approved
0.7586	Intermediate Similarity	NPD6881	Approved
0.7542	Intermediate Similarity	NPD6650	Approved
0.7542	Intermediate Similarity	NPD6649	Approved
0.754	Intermediate Similarity	NPD7078	Approved
0.7523	Intermediate Similarity	NPD6399	Phase 3
0.7521	Intermediate Similarity	NPD6009	Approved
0.75	Intermediate Similarity	NPD5697	Approved
0.75	Intermediate Similarity	NPD6370	Approved
0.748	Intermediate Similarity	NPD6319	Approved
0.7458	Intermediate Similarity	NPD7290	Approved
0.7458	Intermediate Similarity	NPD7102	Approved
0.7458	Intermediate Similarity	NPD6883	Approved
0.7442	Intermediate Similarity	NPD7260	Phase 2
0.744	Intermediate Similarity	NPD7604	Phase 2
0.7436	Intermediate Similarity	NPD6686	Approved
0.7436	Intermediate Similarity	NPD6011	Approved
0.7436	Intermediate Similarity	NPD7320	Approved
0.7431	Intermediate Similarity	NPD6079	Approved
0.7422	Intermediate Similarity	NPD7319	Approved
0.7419	Intermediate Similarity	NPD6016	Approved
0.7419	Intermediate Similarity	NPD5983	Phase 2
0.7419	Intermediate Similarity	NPD6015	Approved
0.7414	Intermediate Similarity	NPD6675	Approved
0.7414	Intermediate Similarity	NPD7128	Approved
0.7414	Intermediate Similarity	NPD6402	Approved
0.7414	Intermediate Similarity	NPD5739	Approved
0.7411	Intermediate Similarity	NPD6083	Phase 2
0.7411	Intermediate Similarity	NPD6084	Phase 2
0.7395	Intermediate Similarity	NPD6847	Approved
0.7395	Intermediate Similarity	NPD8130	Phase 1
0.7395	Intermediate Similarity	NPD6869	Approved
0.7395	Intermediate Similarity	NPD6617	Approved
0.7387	Intermediate Similarity	NPD5695	Phase 3
0.7373	Intermediate Similarity	NPD6014	Approved
0.7373	Intermediate Similarity	NPD6013	Approved
0.7373	Intermediate Similarity	NPD6012	Approved
0.7373	Intermediate Similarity	NPD6373	Approved
0.7373	Intermediate Similarity	NPD6372	Approved
0.736	Intermediate Similarity	NPD5988	Approved
0.735	Intermediate Similarity	NPD6412	Phase 2
0.7345	Intermediate Similarity	NPD4225	Approved
0.7339	Intermediate Similarity	NPD5785	Approved
0.7339	Intermediate Similarity	NPD6059	Approved
0.7339	Intermediate Similarity	NPD5207	Approved
0.7333	Intermediate Similarity	NPD6882	Approved
0.7323	Intermediate Similarity	NPD6336	Discontinued
0.7311	Intermediate Similarity	NPD6371	Approved
0.7304	Intermediate Similarity	NPD5211	Phase 2
0.728	Intermediate Similarity	NPD7503	Approved
0.7273	Intermediate Similarity	NPD5284	Approved
0.7273	Intermediate Similarity	NPD5281	Approved
0.7266	Intermediate Similarity	NPD8293	Discontinued
0.7252	Intermediate Similarity	NPD6845	Suspended
0.7248	Intermediate Similarity	NPD5328	Approved
0.7232	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5779	Approved
0.7207	Intermediate Similarity	NPD5778	Approved
0.7203	Intermediate Similarity	NPD5701	Approved
0.7196	Intermediate Similarity	NPD1694	Approved
0.7193	Intermediate Similarity	NPD5696	Approved
0.7179	Intermediate Similarity	NPD5141	Approved
0.7168	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5221	Approved
0.7168	Intermediate Similarity	NPD5222	Approved
0.7156	Intermediate Similarity	NPD6903	Approved
0.7156	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5737	Approved
0.7156	Intermediate Similarity	NPD6672	Approved
0.7155	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD8513	Phase 3
0.7143	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7334	Approved
0.713	Intermediate Similarity	NPD5330	Approved
0.713	Intermediate Similarity	NPD5286	Approved
0.713	Intermediate Similarity	NPD4696	Approved
0.713	Intermediate Similarity	NPD6409	Approved
0.713	Intermediate Similarity	NPD7146	Approved
0.713	Intermediate Similarity	NPD6684	Approved
0.713	Intermediate Similarity	NPD7521	Approved
0.713	Intermediate Similarity	NPD5285	Approved
0.7117	Intermediate Similarity	NPD5693	Phase 1
0.7107	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5173	Approved
0.7103	Intermediate Similarity	NPD4786	Approved
0.7083	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5210	Approved
0.708	Intermediate Similarity	NPD4629	Approved
0.7069	Intermediate Similarity	NPD5223	Approved
0.7059	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7328	Approved
0.704	Intermediate Similarity	NPD6335	Approved
0.704	Intermediate Similarity	NPD7327	Approved
0.7025	Intermediate Similarity	NPD4634	Approved
0.7025	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4697	Phase 3
0.7016	Intermediate Similarity	NPD6868	Approved
0.7009	Intermediate Similarity	NPD4633	Approved
0.7009	Intermediate Similarity	NPD5226	Approved
0.7009	Intermediate Similarity	NPD5225	Approved
0.7009	Intermediate Similarity	NPD5224	Approved
0.7008	Intermediate Similarity	NPD8033	Approved
0.7008	Intermediate Similarity	NPD8515	Approved
0.7008	Intermediate Similarity	NPD8516	Approved
0.7008	Intermediate Similarity	NPD8517	Approved
0.7	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7748	Approved
0.6984	Remote Similarity	NPD7101	Approved
0.6984	Remote Similarity	NPD7100	Approved
0.6984	Remote Similarity	NPD7516	Approved
0.6972	Remote Similarity	NPD5279	Phase 3
0.6972	Remote Similarity	NPD5690	Phase 2
0.6972	Remote Similarity	NPD3618	Phase 1
0.6964	Remote Similarity	NPD7637	Suspended
0.6964	Remote Similarity	NPD6411	Approved
0.6964	Remote Similarity	NPD7515	Phase 2
0.6964	Remote Similarity	NPD6050	Approved
0.6964	Remote Similarity	NPD5694	Approved
0.696	Remote Similarity	NPD6317	Approved
0.6957	Remote Similarity	NPD7902	Approved
0.6957	Remote Similarity	NPD4755	Approved
0.6949	Remote Similarity	NPD5174	Approved
0.6949	Remote Similarity	NPD5175	Approved
0.6947	Remote Similarity	NPD6033	Approved
0.6944	Remote Similarity	NPD3133	Approved
0.6944	Remote Similarity	NPD3665	Phase 1
0.6944	Remote Similarity	NPD3666	Approved
0.6937	Remote Similarity	NPD6673	Approved
0.6937	Remote Similarity	NPD6904	Approved
0.6937	Remote Similarity	NPD6080	Approved
0.6937	Remote Similarity	NPD4753	Phase 2
0.6929	Remote Similarity	NPD8377	Approved
0.6929	Remote Similarity	NPD8294	Approved
0.6916	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD3667	Approved
0.6909	Remote Similarity	NPD3573	Approved
0.6905	Remote Similarity	NPD6314	Approved
0.6905	Remote Similarity	NPD6313	Approved
0.6897	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5363	Approved
0.688	Remote Similarity	NPD6274	Approved
0.6875	Remote Similarity	NPD46	Approved
0.6875	Remote Similarity	NPD8378	Approved
0.6875	Remote Similarity	NPD8380	Approved
0.6875	Remote Similarity	NPD8335	Approved
0.6875	Remote Similarity	NPD8379	Approved
0.6875	Remote Similarity	NPD8296	Approved
0.6875	Remote Similarity	NPD6698	Approved
0.6875	Remote Similarity	NPD5692	Phase 3
0.6857	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5362	Discontinued
0.6842	Remote Similarity	NPD6001	Approved
0.6838	Remote Similarity	NPD4700	Approved
0.6818	Remote Similarity	NPD5786	Approved
0.6786	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6101	Approved
0.6786	Remote Similarity	NPD6051	Approved
0.678	Remote Similarity	NPD5344	Discontinued
0.6777	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD8328	Phase 3
0.6759	Remote Similarity	NPD4221	Approved
0.6759	Remote Similarity	NPD4223	Phase 3
0.6754	Remote Similarity	NPD4202	Approved
0.6727	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5329	Approved
0.6721	Remote Similarity	NPD4730	Approved
0.6721	Remote Similarity	NPD4729	Approved
0.672	Remote Similarity	NPD8133	Approved
0.6716	Remote Similarity	NPD5956	Approved
0.6696	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5282	Discontinued
0.6696	Remote Similarity	NPD7900	Approved
0.6696	Remote Similarity	NPD5208	Approved
0.6695	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	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