NPASS Compound

Structure

NPC470961 OpenBabel07101718192D 34 38 0 0 1 0 0 0 0 0999 V2000 -1.5645 4.8151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1514 1.4402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4117 2.6007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6772 0.8546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9432 3.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9432 2.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0994 3.5751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0994 0.6520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2555 0.1648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5679 2.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3653 -0.7883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7241 1.6263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3963 -0.8901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0430 3.2101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2888 5.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8404 4.1631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0994 1.6263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4117 0.6520 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0862 4.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5679 0.1648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4117 1.6263 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2555 3.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3189 2.5581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8103 3.8123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7241 0.6520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2555 2.1135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7241 0.6520 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 -0.4353 6.0693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4117 3.5751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7370 4.1134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3761 -0.0721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9267 -0.3011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6077 2.8592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 25 1 0 0 0 0 5 6 1 0 0 0 0 5 7 2 0 0 0 0 6 17 1 0 0 0 0 7 22 1 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 20 2 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 19 1 0 0 0 0 15 29 1 0 0 0 0 16 19 2 0 0 0 0 17 26 1 0 0 0 0 18 9 1 1 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 6 0 0 0 22 26 1 0 0 0 0 22 30 2 0 0 0 0 23 27 1 1 0 0 0 23 34 1 0 0 0 0 24 31 2 0 0 0 0 24 34 1 0 0 0 0 25 28 1 1 0 0 0 26 3 1 6 0 0 0 27 4 1 6 0 0 0 27 28 1 0 0 0 0 27 32 1 0 0 0 0 28 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.16
Volume:	386.309
LogP:	3.077
LogD:	3.04
LogS:	-4.605
# Rotatable Bonds:	8
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.653
Synthetic Accessibility Score:	2.29
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.757
MDCK Permeability:	4.0752354834694415e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.975
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.319

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	82.85759735107422%
Volume Distribution (VD):	0.612
Pgp-substrate:	14.576787948608398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.316
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.435
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.248
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.618
CYP3A4-substrate:	0.862

ADMET: Excretion

Clearance (CL):	8.506
Half-life (T1/2):	0.79

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.835
AMES Toxicity:	0.14
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.072
Skin Sensitization:	0.134
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.044
Respiratory Toxicity:	0.377

Download Data

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

Natural Product: NPC470961

Natural Product ID:	NPC470961
*Common Name:**	Withacoagulin H
IUPAC Name:	(2R)-2-[(1S)-1-hydroxy-1-[(8R,9S,10R,13S,17R)-17-hydroxy-10,13-dimethyl-1-oxo-7,8,9,11,12,16-hexahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
Synonyms:	Withacoagulin H
Standard InCHIKey:	UNWUYUBEZUQEBC-DREDRYRMSA-N
Standard InCHI:	InChI=1S/C28H36O6/c1-16-14-23(34-24(31)19(16)15-29)27(4,32)28(33)13-11-20-18-9-8-17-6-5-7-22(30)26(17,3)21(18)10-12-25(20,28)2/h5,7-8,11,18,21,23,29,32-33H,6,9-10,12-15H2,1-4H3/t18-,21-,23+,25-,26-,27-,28+/m0/s1
SMILES:	OCC1=C(C)C[C@@H](OC1=O)[C@@]([C@@]1(O)CC=C2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)C(=O)C=CC2)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333672
PubChem CID:	71524298
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
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[18952419]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23316950]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13927	Withania coagulans	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	2
Others	4

Activity Type	# Activity
Cell Line	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	3100.0	nM	PMID[551859]
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	90.3	%	PMID[551859]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	70.4	%	PMID[551859]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	100.0	%	PMID[551859]
NPT2	Others	Unspecified		IC50	=	5000.0	nM	PMID[551859]
NPT2	Others	Unspecified		Inhibition	=	98.3	%	PMID[551859]

☑ 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 NPC470961 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	207
0.1-0.2	1102
0.2-0.3	3661
0.3-0.4	7297
0.4-0.5	13740
0.5-0.6	7590
0.6-0.7	6767
0.7-0.8	2215
0.8-0.85	87
0.85-0.9	26
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9902	High Similarity	NPC29133
0.9712	High Similarity	NPC191620
0.9266	High Similarity	NPC186525
0.9259	High Similarity	NPC64318
0.9231	High Similarity	NPC91034
0.9174	High Similarity	NPC183580
0.9174	High Similarity	NPC312824
0.9174	High Similarity	NPC470493
0.9151	High Similarity	NPC37116
0.9018	High Similarity	NPC46570
0.9009	High Similarity	NPC264954
0.9	High Similarity	NPC286528
0.9	High Similarity	NPC140055
0.9	High Similarity	NPC470492
0.9	High Similarity	NPC20302
0.9	High Similarity	NPC167606
0.8991	High Similarity	NPC147912
0.8991	High Similarity	NPC67259
0.8981	High Similarity	NPC236217
0.8962	High Similarity	NPC220155
0.8938	High Similarity	NPC107493
0.8929	High Similarity	NPC474370
0.8919	High Similarity	NPC709
0.8919	High Similarity	NPC50774
0.8909	High Similarity	NPC176840
0.8796	High Similarity	NPC473627
0.8772	High Similarity	NPC88326
0.8772	High Similarity	NPC153700
0.8727	High Similarity	NPC122056
0.8716	High Similarity	NPC474315
0.8684	High Similarity	NPC67569
0.8649	High Similarity	NPC474181
0.8621	High Similarity	NPC8374
0.8609	High Similarity	NPC470265
0.8609	High Similarity	NPC23786
0.8596	High Similarity	NPC79579
0.8584	High Similarity	NPC153440
0.8571	High Similarity	NPC190286
0.8545	High Similarity	NPC324683
0.8534	High Similarity	NPC469789
0.8522	High Similarity	NPC473256
0.8522	High Similarity	NPC470878
0.8509	High Similarity	NPC473274
0.8509	High Similarity	NPC5292
0.8509	High Similarity	NPC473270
0.8462	Intermediate Similarity	NPC172154
0.8462	Intermediate Similarity	NPC8369
0.8462	Intermediate Similarity	NPC3381
0.8462	Intermediate Similarity	NPC81736
0.8462	Intermediate Similarity	NPC470494
0.8435	Intermediate Similarity	NPC474585
0.8421	Intermediate Similarity	NPC329736
0.8421	Intermediate Similarity	NPC475913
0.8407	Intermediate Similarity	NPC270929
0.839	Intermediate Similarity	NPC293112
0.8376	Intermediate Similarity	NPC11895
0.8364	Intermediate Similarity	NPC475065
0.835	Intermediate Similarity	NPC53685
0.8349	Intermediate Similarity	NPC329048
0.8349	Intermediate Similarity	NPC330011
0.8348	Intermediate Similarity	NPC474179
0.8348	Intermediate Similarity	NPC270850
0.8348	Intermediate Similarity	NPC475834
0.8348	Intermediate Similarity	NPC61520
0.8348	Intermediate Similarity	NPC305260
0.8333	Intermediate Similarity	NPC476965
0.8333	Intermediate Similarity	NPC470959
0.8333	Intermediate Similarity	NPC303697
0.8333	Intermediate Similarity	NPC243065
0.8333	Intermediate Similarity	NPC473175
0.8319	Intermediate Similarity	NPC287903
0.8304	Intermediate Similarity	NPC221144
0.8304	Intermediate Similarity	NPC69291
0.8302	Intermediate Similarity	NPC474012
0.8302	Intermediate Similarity	NPC476299
0.8291	Intermediate Similarity	NPC170538
0.8291	Intermediate Similarity	NPC269642
0.8273	Intermediate Similarity	NPC473482
0.8273	Intermediate Similarity	NPC318363
0.8273	Intermediate Similarity	NPC472825
0.8273	Intermediate Similarity	NPC475418
0.8252	Intermediate Similarity	NPC115021
0.8241	Intermediate Similarity	NPC470954
0.8224	Intermediate Similarity	NPC469657
0.8224	Intermediate Similarity	NPC473174
0.8224	Intermediate Similarity	NPC99411
0.8224	Intermediate Similarity	NPC244456
0.822	Intermediate Similarity	NPC473979
0.8208	Intermediate Similarity	NPC316598
0.8208	Intermediate Similarity	NPC235464
0.8208	Intermediate Similarity	NPC98868
0.8208	Intermediate Similarity	NPC197386
0.8208	Intermediate Similarity	NPC166745
0.8198	Intermediate Similarity	NPC41405
0.819	Intermediate Similarity	NPC475041
0.8182	Intermediate Similarity	NPC473284
0.8182	Intermediate Similarity	NPC473593
0.8182	Intermediate Similarity	NPC475294
0.8174	Intermediate Similarity	NPC239273
0.8167	Intermediate Similarity	NPC156797
0.8165	Intermediate Similarity	NPC296950
0.8165	Intermediate Similarity	NPC146731
0.8158	Intermediate Similarity	NPC284915
0.8158	Intermediate Similarity	NPC470953
0.8148	Intermediate Similarity	NPC473163
0.8148	Intermediate Similarity	NPC475320
0.8142	Intermediate Similarity	NPC475524
0.8142	Intermediate Similarity	NPC470063
0.8142	Intermediate Similarity	NPC100267
0.812	Intermediate Similarity	NPC476961
0.8113	Intermediate Similarity	NPC53844
0.8113	Intermediate Similarity	NPC476253
0.8103	Intermediate Similarity	NPC257457
0.8103	Intermediate Similarity	NPC311554
0.8099	Intermediate Similarity	NPC245094
0.8095	Intermediate Similarity	NPC171395
0.8087	Intermediate Similarity	NPC148458
0.8083	Intermediate Similarity	NPC473635
0.8077	Intermediate Similarity	NPC474736
0.8073	Intermediate Similarity	NPC476889
0.8073	Intermediate Similarity	NPC475050
0.8056	Intermediate Similarity	NPC310981
0.8056	Intermediate Similarity	NPC472924
0.8049	Intermediate Similarity	NPC231240
0.8037	Intermediate Similarity	NPC478056
0.8037	Intermediate Similarity	NPC471717
0.8036	Intermediate Similarity	NPC472216
0.8036	Intermediate Similarity	NPC137911
0.8036	Intermediate Similarity	NPC284828
0.8036	Intermediate Similarity	NPC173905
0.8036	Intermediate Similarity	NPC228477
0.8036	Intermediate Similarity	NPC47951
0.8036	Intermediate Similarity	NPC5475
0.8033	Intermediate Similarity	NPC231529
0.8033	Intermediate Similarity	NPC476966
0.8019	Intermediate Similarity	NPC328371
0.8019	Intermediate Similarity	NPC117133
0.8019	Intermediate Similarity	NPC456
0.8019	Intermediate Similarity	NPC472941
0.8018	Intermediate Similarity	NPC144459
0.8017	Intermediate Similarity	NPC284068
0.8017	Intermediate Similarity	NPC471854
0.8	Intermediate Similarity	NPC472868
0.8	Intermediate Similarity	NPC13385
0.8	Intermediate Similarity	NPC318135
0.7984	Intermediate Similarity	NPC316915
0.7982	Intermediate Similarity	NPC473424
0.7982	Intermediate Similarity	NPC40918
0.7982	Intermediate Similarity	NPC476890
0.7982	Intermediate Similarity	NPC269530
0.7981	Intermediate Similarity	NPC177037
0.7981	Intermediate Similarity	NPC472814
0.7967	Intermediate Similarity	NPC196921
0.7967	Intermediate Similarity	NPC220757
0.7966	Intermediate Similarity	NPC476962
0.7965	Intermediate Similarity	NPC5103
0.7965	Intermediate Similarity	NPC235014
0.7965	Intermediate Similarity	NPC5284
0.7963	Intermediate Similarity	NPC54705
0.7961	Intermediate Similarity	NPC5509
0.7949	Intermediate Similarity	NPC288679
0.7946	Intermediate Similarity	NPC177064
0.7946	Intermediate Similarity	NPC151393
0.7944	Intermediate Similarity	NPC253826
0.7944	Intermediate Similarity	NPC156546
0.7944	Intermediate Similarity	NPC107243
0.7944	Intermediate Similarity	NPC202705
0.7931	Intermediate Similarity	NPC470075
0.7931	Intermediate Similarity	NPC476963
0.7928	Intermediate Similarity	NPC266570
0.7928	Intermediate Similarity	NPC472935
0.7928	Intermediate Similarity	NPC477125
0.7928	Intermediate Similarity	NPC189863
0.7928	Intermediate Similarity	NPC60681
0.7925	Intermediate Similarity	NPC472932
0.7925	Intermediate Similarity	NPC318282
0.7925	Intermediate Similarity	NPC209355
0.7925	Intermediate Similarity	NPC469995
0.7925	Intermediate Similarity	NPC33473
0.7925	Intermediate Similarity	NPC173875
0.7925	Intermediate Similarity	NPC174948
0.7917	Intermediate Similarity	NPC204812
0.7917	Intermediate Similarity	NPC120724
0.7913	Intermediate Similarity	NPC255017
0.7913	Intermediate Similarity	NPC25909
0.7913	Intermediate Similarity	NPC469454
0.7913	Intermediate Similarity	NPC469496
0.7913	Intermediate Similarity	NPC469463
0.7909	Intermediate Similarity	NPC111323
0.7909	Intermediate Similarity	NPC95899
0.7909	Intermediate Similarity	NPC474207
0.7909	Intermediate Similarity	NPC475526
0.7909	Intermediate Similarity	NPC72151
0.7909	Intermediate Similarity	NPC236390
0.7909	Intermediate Similarity	NPC264048
0.7909	Intermediate Similarity	NPC474330
0.7909	Intermediate Similarity	NPC329345
0.7909	Intermediate Similarity	NPC473283
0.7909	Intermediate Similarity	NPC26478
0.7909	Intermediate Similarity	NPC324001

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 NPC470961 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1384
0.2-0.3	3385
0.3-0.4	2644
0.4-0.5	1007
0.5-0.6	289
0.6-0.7	237
0.7-0.8	23
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
0.9	High Similarity	NPD7115	Discovery
0.787	Intermediate Similarity	NPD4225	Approved
0.7807	Intermediate Similarity	NPD6371	Approved
0.7778	Intermediate Similarity	NPD6083	Phase 2
0.7778	Intermediate Similarity	NPD6084	Phase 2
0.7757	Intermediate Similarity	NPD5695	Phase 3
0.7714	Intermediate Similarity	NPD5785	Approved
0.7672	Intermediate Similarity	NPD8297	Approved
0.7632	Intermediate Similarity	NPD6899	Approved
0.7632	Intermediate Similarity	NPD6881	Approved
0.7544	Intermediate Similarity	NPD5697	Approved
0.7521	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD7290	Approved
0.7478	Intermediate Similarity	NPD6686	Approved
0.7477	Intermediate Similarity	NPD7640	Approved
0.7477	Intermediate Similarity	NPD7639	Approved
0.7456	Intermediate Similarity	NPD6675	Approved
0.7456	Intermediate Similarity	NPD7128	Approved
0.7456	Intermediate Similarity	NPD6402	Approved
0.7456	Intermediate Similarity	NPD5739	Approved
0.7436	Intermediate Similarity	NPD6617	Approved
0.7436	Intermediate Similarity	NPD8130	Phase 1
0.7436	Intermediate Similarity	NPD6869	Approved
0.7436	Intermediate Similarity	NPD6649	Approved
0.7436	Intermediate Similarity	NPD6847	Approved
0.7436	Intermediate Similarity	NPD6650	Approved
0.7414	Intermediate Similarity	NPD6013	Approved
0.7414	Intermediate Similarity	NPD6014	Approved
0.7414	Intermediate Similarity	NPD6012	Approved
0.7407	Intermediate Similarity	NPD6399	Phase 3
0.7391	Intermediate Similarity	NPD6412	Phase 2
0.7387	Intermediate Similarity	NPD5696	Approved
0.7387	Intermediate Similarity	NPD7638	Approved
0.7373	Intermediate Similarity	NPD6053	Discontinued
0.7373	Intermediate Similarity	NPD6882	Approved
0.7358	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5211	Phase 2
0.7333	Intermediate Similarity	NPD7521	Approved
0.7333	Intermediate Similarity	NPD7334	Approved
0.7333	Intermediate Similarity	NPD5330	Approved
0.7333	Intermediate Similarity	NPD7146	Approved
0.7333	Intermediate Similarity	NPD6409	Approved
0.7333	Intermediate Similarity	NPD6684	Approved
0.7328	Intermediate Similarity	NPD6011	Approved
0.7328	Intermediate Similarity	NPD7320	Approved
0.7323	Intermediate Similarity	NPD7319	Approved
0.7317	Intermediate Similarity	NPD7503	Approved
0.7315	Intermediate Similarity	NPD6411	Approved
0.7315	Intermediate Similarity	NPD5281	Approved
0.7315	Intermediate Similarity	NPD5284	Approved
0.7315	Intermediate Similarity	NPD5693	Phase 1
0.7311	Intermediate Similarity	NPD4632	Approved
0.729	Intermediate Similarity	NPD4753	Phase 2
0.728	Intermediate Similarity	NPD7492	Approved
0.7273	Intermediate Similarity	NPD5210	Approved
0.7273	Intermediate Similarity	NPD4629	Approved
0.7273	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD6372	Approved
0.7265	Intermediate Similarity	NPD6373	Approved
0.7248	Intermediate Similarity	NPD5778	Approved
0.7248	Intermediate Similarity	NPD5779	Approved
0.7244	Intermediate Similarity	NPD7736	Approved
0.7241	Intermediate Similarity	NPD5701	Approved
0.7241	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5363	Approved
0.7236	Intermediate Similarity	NPD6054	Approved
0.7222	Intermediate Similarity	NPD7507	Approved
0.7222	Intermediate Similarity	NPD6616	Approved
0.7217	Intermediate Similarity	NPD5141	Approved
0.7203	Intermediate Similarity	NPD4634	Approved
0.7196	Intermediate Similarity	NPD6672	Approved
0.7196	Intermediate Similarity	NPD6903	Approved
0.7196	Intermediate Similarity	NPD5737	Approved
0.7182	Intermediate Similarity	NPD7748	Approved
0.717	Intermediate Similarity	NPD5690	Phase 2
0.7168	Intermediate Similarity	NPD5286	Approved
0.7168	Intermediate Similarity	NPD4696	Approved
0.7168	Intermediate Similarity	NPD5285	Approved
0.7165	Intermediate Similarity	NPD7078	Approved
0.7156	Intermediate Similarity	NPD6050	Approved
0.7156	Intermediate Similarity	NPD7515	Phase 2
0.7156	Intermediate Similarity	NPD6079	Approved
0.7156	Intermediate Similarity	NPD7637	Suspended
0.7156	Intermediate Similarity	NPD5694	Approved
0.7143	Intermediate Similarity	NPD4786	Approved
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD3666	Approved
0.713	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6673	Approved
0.713	Intermediate Similarity	NPD6101	Approved
0.713	Intermediate Similarity	NPD6904	Approved
0.713	Intermediate Similarity	NPD6080	Approved
0.712	Intermediate Similarity	NPD6370	Approved
0.7119	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1694	Approved
0.7064	Intermediate Similarity	NPD5692	Phase 3
0.7064	Intermediate Similarity	NPD5207	Approved
0.7048	Intermediate Similarity	NPD5362	Discontinued
0.7048	Intermediate Similarity	NPD7154	Phase 3
0.7043	Intermediate Similarity	NPD5226	Approved
0.7043	Intermediate Similarity	NPD5224	Approved
0.7043	Intermediate Similarity	NPD5225	Approved
0.7043	Intermediate Similarity	NPD4633	Approved
0.704	Intermediate Similarity	NPD6015	Approved
0.704	Intermediate Similarity	NPD6016	Approved
0.7016	Intermediate Similarity	NPD7101	Approved
0.7016	Intermediate Similarity	NPD7100	Approved
0.7009	Intermediate Similarity	NPD5279	Phase 3
0.7009	Intermediate Similarity	NPD4623	Approved
0.7009	Intermediate Similarity	NPD4519	Discontinued
0.7	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6009	Approved
0.6991	Remote Similarity	NPD4755	Approved
0.6991	Remote Similarity	NPD7902	Approved
0.6984	Remote Similarity	NPD5988	Approved
0.6983	Remote Similarity	NPD5175	Approved
0.6983	Remote Similarity	NPD5174	Approved
0.6972	Remote Similarity	NPD5328	Approved
0.6972	Remote Similarity	NPD6051	Approved
0.6964	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6059	Approved
0.6957	Remote Similarity	NPD5223	Approved
0.6952	Remote Similarity	NPD4270	Approved
0.6952	Remote Similarity	NPD3667	Approved
0.6952	Remote Similarity	NPD4223	Phase 3
0.6952	Remote Similarity	NPD4269	Approved
0.6952	Remote Similarity	NPD4221	Approved
0.6937	Remote Similarity	NPD4202	Approved
0.6935	Remote Similarity	NPD7327	Approved
0.6935	Remote Similarity	NPD6335	Approved
0.6935	Remote Similarity	NPD7328	Approved
0.6929	Remote Similarity	NPD7604	Phase 2
0.6916	Remote Similarity	NPD5329	Approved
0.6911	Remote Similarity	NPD6274	Approved
0.6909	Remote Similarity	NPD46	Approved
0.6909	Remote Similarity	NPD6698	Approved
0.6905	Remote Similarity	NPD8033	Approved
0.6905	Remote Similarity	NPD5983	Phase 2
0.6905	Remote Similarity	NPD8513	Phase 3
0.6903	Remote Similarity	NPD5221	Approved
0.6903	Remote Similarity	NPD5222	Approved
0.6903	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD8293	Discontinued
0.6897	Remote Similarity	NPD7632	Discontinued
0.6893	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5208	Approved
0.688	Remote Similarity	NPD7516	Approved
0.687	Remote Similarity	NPD4700	Approved
0.686	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5369	Approved
0.6855	Remote Similarity	NPD6317	Approved
0.6852	Remote Similarity	NPD5786	Approved
0.6852	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3618	Phase 1
0.6852	Remote Similarity	NPD6098	Approved
0.6852	Remote Similarity	NPD5280	Approved
0.6852	Remote Similarity	NPD4694	Approved
0.6842	Remote Similarity	NPD5173	Approved
0.6825	Remote Similarity	NPD8294	Approved
0.6825	Remote Similarity	NPD8377	Approved
0.6822	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6336	Discontinued
0.6822	Remote Similarity	NPD4197	Approved
0.6818	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5344	Discontinued
0.68	Remote Similarity	NPD6313	Approved
0.68	Remote Similarity	NPD6314	Approved
0.6789	Remote Similarity	NPD3573	Approved
0.6777	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6868	Approved
0.6772	Remote Similarity	NPD8380	Approved
0.6772	Remote Similarity	NPD8379	Approved
0.6772	Remote Similarity	NPD8516	Approved
0.6772	Remote Similarity	NPD8378	Approved
0.6772	Remote Similarity	NPD8296	Approved
0.6772	Remote Similarity	NPD8517	Approved
0.6772	Remote Similarity	NPD8335	Approved
0.6772	Remote Similarity	NPD8515	Approved
0.6762	Remote Similarity	NPD4252	Approved
0.675	Remote Similarity	NPD4730	Approved
0.675	Remote Similarity	NPD4729	Approved
0.6748	Remote Similarity	NPD8133	Approved
0.6746	Remote Similarity	NPD4522	Approved
0.6729	Remote Similarity	NPD4788	Approved
0.6726	Remote Similarity	NPD7900	Approved
0.6726	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6404	Discontinued
0.6723	Remote Similarity	NPD6008	Approved
0.6697	Remote Similarity	NPD4689	Approved
0.6697	Remote Similarity	NPD4690	Approved
0.6697	Remote Similarity	NPD4693	Phase 3
0.6697	Remote Similarity	NPD5205	Approved
0.6697	Remote Similarity	NPD4688	Approved
0.6697	Remote Similarity	NPD4138	Approved
0.6696	Remote Similarity	NPD7983	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