NPASS Compound

Structure

NPC471854 OpenBabel07101719132D 40 43 0 0 1 0 0 0 0 0999 V2000 -2.5388 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9855 2.6396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2424 3.3087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 1.9292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 0.3872 1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0563 2.5385 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 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0345 2.3305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 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 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.0388 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3435 1.3795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2111 0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 9 32 1 0 0 0 0 10 11 1 0 0 0 0 10 18 2 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 15 29 1 0 0 0 0 16 24 1 0 0 0 0 16 30 1 0 0 0 0 17 33 2 0 0 0 0 17 40 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 31 1 6 0 0 0 20 26 1 0 0 0 0 20 34 1 6 0 0 0 21 25 1 0 0 0 0 21 40 1 1 0 0 0 22 29 1 1 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 23 35 2 0 0 0 0 24 31 1 0 0 0 0 24 36 2 0 0 0 0 25 30 1 6 0 0 0 25 32 1 0 0 0 0 26 28 1 0 0 0 0 26 37 1 1 0 0 0 27 38 1 0 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 31 8 1 6 0 0 0 32 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.33
Volume:	584.942
LogP:	2.872
LogD:	2.842
LogS:	-4.172
# Rotatable Bonds:	6
TPSA:	141.36
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.228
Synthetic Accessibility Score:	5.439
Fsp3:	0.781
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.047
MDCK Permeability:	1.3370532542467117e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.105
Human Intestinal Absorption (HIA):	0.077
20% Bioavailability (F20%):	0.084
30% Bioavailability (F30%):	0.188

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.821
Plasma Protein Binding (PPB):	65.28640747070312%
Volume Distribution (VD):	0.478
Pgp-substrate:	19.67964744567871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.595
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.603
CYP3A4-substrate:	0.583

ADMET: Excretion

Clearance (CL):	3.091
Half-life (T1/2):	0.453

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.243
Drug-inuced Liver Injury (DILI):	0.237
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.807
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.103
Carcinogencity:	0.893
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.715

Download Data

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

Natural Product: NPC471854

Natural Product ID:	NPC471854
*Common Name:**	2Beta,3Alpha,16Alpha,20,25-Tetrahydroxycucurbita-5,23(E)-Diene-11,22-Dione-16-Acetate
IUPAC Name:	[(2S,3S,8S,9R,10R,13R,14S,16R,17R)-17-[(E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,3-dihydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl] acetate
Synonyms:
Standard InCHIKey:	PKTPBFBNOBGLCY-MZRCPWCYSA-N
Standard InCHI:	InChI=1S/C32H48O8/c1-17(33)40-21-15-29(6)22-11-10-18-19(14-20(34)26(37)28(18,4)5)31(22,8)24(36)16-30(29,7)25(21)32(9,39)23(35)12-13-27(2,3)38/h10,12-13,19-22,25-26,34,37-39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,26-,29+,30-,31+,32?/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@@]2([C@]([C@H]1C(C(=O)/C=C/C(O)(C)C)(O)C)(C)CC(=O)[C@@]1([C@H]2CC=C2[C@H]1C[C@@H]([C@H](C2(C)C)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3261680
PubChem CID:	90676075
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO33474	hemsleya penxianensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717151]

☑ 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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	0.42	ug.mL-1	PMID[515046]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	0.44	ug.mL-1	PMID[515046]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.43	ug.mL-1	PMID[515046]

☑ 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 NPC471854 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	228
0.1-0.2	1223
0.2-0.3	3948
0.3-0.4	8104
0.4-0.5	12680
0.5-0.6	6718
0.6-0.7	6420
0.7-0.8	2919
0.8-0.85	357
0.85-0.9	86
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9725	High Similarity	NPC257457
0.9725	High Similarity	NPC311554
0.9346	High Similarity	NPC214644
0.9266	High Similarity	NPC475524
0.9266	High Similarity	NPC100267
0.9189	High Similarity	NPC148458
0.9091	High Similarity	NPC280782
0.9043	High Similarity	NPC222688
0.9009	High Similarity	NPC250109
0.9009	High Similarity	NPC962
0.8938	High Similarity	NPC239273
0.8919	High Similarity	NPC221144
0.8898	High Similarity	NPC470882
0.8879	High Similarity	NPC311612
0.887	High Similarity	NPC109973
0.886	High Similarity	NPC329736
0.885	High Similarity	NPC49492
0.885	High Similarity	NPC266728
0.8839	High Similarity	NPC108721
0.8839	High Similarity	NPC73300
0.8807	High Similarity	NPC185
0.8807	High Similarity	NPC475294
0.8807	High Similarity	NPC44063
0.8785	High Similarity	NPC477915
0.8785	High Similarity	NPC87351
0.8783	High Similarity	NPC61520
0.8761	High Similarity	NPC147912
0.8761	High Similarity	NPC67259
0.876	High Similarity	NPC471855
0.875	High Similarity	NPC147180
0.875	High Similarity	NPC264634
0.875	High Similarity	NPC71348
0.8739	High Similarity	NPC473265
0.8716	High Similarity	NPC149047
0.8684	High Similarity	NPC270958
0.8684	High Similarity	NPC270929
0.8661	High Similarity	NPC43775
0.8649	High Similarity	NPC11710
0.8649	High Similarity	NPC2766
0.8636	High Similarity	NPC220229
0.8636	High Similarity	NPC475060
0.8636	High Similarity	NPC83744
0.8636	High Similarity	NPC477916
0.8624	High Similarity	NPC209502
0.8624	High Similarity	NPC204833
0.8621	High Similarity	NPC472933
0.8621	High Similarity	NPC264954
0.8621	High Similarity	NPC475041
0.8611	High Similarity	NPC136289
0.8611	High Similarity	NPC473424
0.8609	High Similarity	NPC470959
0.8609	High Similarity	NPC472934
0.8609	High Similarity	NPC476965
0.8595	High Similarity	NPC471407
0.8595	High Similarity	NPC470880
0.8584	High Similarity	NPC207251
0.8583	High Similarity	NPC473253
0.8571	High Similarity	NPC473255
0.8571	High Similarity	NPC76084
0.8559	High Similarity	NPC217201
0.8559	High Similarity	NPC269642
0.8559	High Similarity	NPC329417
0.8559	High Similarity	NPC295244
0.8547	High Similarity	NPC474370
0.8545	High Similarity	NPC171137
0.8545	High Similarity	NPC152695
0.8545	High Similarity	NPC260268
0.8545	High Similarity	NPC476027
0.8545	High Similarity	NPC150531
0.8545	High Similarity	NPC50692
0.8545	High Similarity	NPC85829
0.8545	High Similarity	NPC48733
0.8545	High Similarity	NPC319077
0.8545	High Similarity	NPC97202
0.8545	High Similarity	NPC296945
0.8545	High Similarity	NPC257353
0.8545	High Similarity	NPC49958
0.8545	High Similarity	NPC196528
0.8545	High Similarity	NPC302607
0.8545	High Similarity	NPC202167
0.8545	High Similarity	NPC181265
0.8545	High Similarity	NPC214264
0.8534	High Similarity	NPC118638
0.8532	High Similarity	NPC191892
0.8532	High Similarity	NPC111323
0.8532	High Similarity	NPC264048
0.8519	High Similarity	NPC476240
0.8519	High Similarity	NPC224720
0.8519	High Similarity	NPC476223
0.8519	High Similarity	NPC81530
0.8509	High Similarity	NPC472929
0.8509	High Similarity	NPC202889
0.8509	High Similarity	NPC472926
0.8509	High Similarity	NPC317210
0.8487	Intermediate Similarity	NPC473979
0.8482	Intermediate Similarity	NPC241927
0.8482	Intermediate Similarity	NPC258543
0.8482	Intermediate Similarity	NPC41405
0.8482	Intermediate Similarity	NPC304495
0.8468	Intermediate Similarity	NPC473284
0.8468	Intermediate Similarity	NPC165873
0.8462	Intermediate Similarity	NPC473270
0.8455	Intermediate Similarity	NPC137657
0.8455	Intermediate Similarity	NPC235889
0.8448	Intermediate Similarity	NPC470492
0.8448	Intermediate Similarity	NPC286528
0.8448	Intermediate Similarity	NPC20302
0.8448	Intermediate Similarity	NPC472927
0.8448	Intermediate Similarity	NPC140055
0.8448	Intermediate Similarity	NPC167606
0.8443	Intermediate Similarity	NPC231529
0.844	Intermediate Similarity	NPC119601
0.844	Intermediate Similarity	NPC308726
0.844	Intermediate Similarity	NPC473928
0.8435	Intermediate Similarity	NPC326542
0.8426	Intermediate Similarity	NPC476274
0.8426	Intermediate Similarity	NPC316964
0.8426	Intermediate Similarity	NPC144956
0.8421	Intermediate Similarity	NPC170487
0.8417	Intermediate Similarity	NPC81736
0.8417	Intermediate Similarity	NPC172154
0.8407	Intermediate Similarity	NPC37116
0.8407	Intermediate Similarity	NPC239097
0.8407	Intermediate Similarity	NPC5284
0.8407	Intermediate Similarity	NPC197428
0.8407	Intermediate Similarity	NPC473627
0.8403	Intermediate Similarity	NPC88326
0.8403	Intermediate Similarity	NPC28532
0.8403	Intermediate Similarity	NPC153700
0.8393	Intermediate Similarity	NPC472218
0.8393	Intermediate Similarity	NPC472219
0.8393	Intermediate Similarity	NPC472825
0.8393	Intermediate Similarity	NPC65941
0.8393	Intermediate Similarity	NPC472217
0.839	Intermediate Similarity	NPC476961
0.8378	Intermediate Similarity	NPC323834
0.8376	Intermediate Similarity	NPC50774
0.8376	Intermediate Similarity	NPC709
0.8374	Intermediate Similarity	NPC196921
0.8374	Intermediate Similarity	NPC220757
0.8364	Intermediate Similarity	NPC236390
0.8364	Intermediate Similarity	NPC247957
0.8364	Intermediate Similarity	NPC249187
0.8362	Intermediate Similarity	NPC64318
0.8349	Intermediate Similarity	NPC115899
0.8349	Intermediate Similarity	NPC163372
0.8349	Intermediate Similarity	NPC302537
0.8348	Intermediate Similarity	NPC122056
0.8348	Intermediate Similarity	NPC194100
0.8347	Intermediate Similarity	NPC15095
0.8347	Intermediate Similarity	NPC293112
0.8347	Intermediate Similarity	NPC473635
0.8333	Intermediate Similarity	NPC11895
0.8333	Intermediate Similarity	NPC472928
0.8333	Intermediate Similarity	NPC469789
0.8333	Intermediate Similarity	NPC214797
0.8333	Intermediate Similarity	NPC118860
0.8333	Intermediate Similarity	NPC197386
0.8333	Intermediate Similarity	NPC231589
0.8319	Intermediate Similarity	NPC46570
0.8319	Intermediate Similarity	NPC475941
0.8319	Intermediate Similarity	NPC474901
0.8305	Intermediate Similarity	NPC5292
0.8304	Intermediate Similarity	NPC220974
0.8304	Intermediate Similarity	NPC471783
0.8304	Intermediate Similarity	NPC9457
0.8304	Intermediate Similarity	NPC472925
0.8293	Intermediate Similarity	NPC35109
0.8291	Intermediate Similarity	NPC243065
0.8291	Intermediate Similarity	NPC470493
0.8291	Intermediate Similarity	NPC312824
0.8291	Intermediate Similarity	NPC284068
0.8291	Intermediate Similarity	NPC183580
0.8288	Intermediate Similarity	NPC75531
0.8288	Intermediate Similarity	NPC118911
0.8288	Intermediate Similarity	NPC149124
0.8273	Intermediate Similarity	NPC195290
0.8273	Intermediate Similarity	NPC56498
0.8273	Intermediate Similarity	NPC204450
0.8264	Intermediate Similarity	NPC3381
0.8264	Intermediate Similarity	NPC8369
0.8264	Intermediate Similarity	NPC8374
0.8261	Intermediate Similarity	NPC475970
0.8261	Intermediate Similarity	NPC191620
0.8261	Intermediate Similarity	NPC234042
0.8261	Intermediate Similarity	NPC152117
0.8257	Intermediate Similarity	NPC266955
0.825	Intermediate Similarity	NPC470265
0.825	Intermediate Similarity	NPC107493
0.825	Intermediate Similarity	NPC170538
0.825	Intermediate Similarity	NPC23786
0.8246	Intermediate Similarity	NPC129689
0.8241	Intermediate Similarity	NPC18509
0.8241	Intermediate Similarity	NPC107243
0.824	Intermediate Similarity	NPC469673
0.8235	Intermediate Similarity	NPC79579
0.8235	Intermediate Similarity	NPC471406
0.823	Intermediate Similarity	NPC177064
0.823	Intermediate Similarity	NPC94529
0.8224	Intermediate Similarity	NPC469599

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 NPC471854 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1428
0.2-0.3	3655
0.3-0.4	2538
0.4-0.5	795
0.5-0.6	228
0.6-0.7	153
0.7-0.8	91
0.8-0.85	37
0.85-0.9	29
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD8297	Approved
0.9	High Similarity	NPD6649	Approved
0.9	High Similarity	NPD6650	Approved
0.8899	High Similarity	NPD6899	Approved
0.8899	High Similarity	NPD6881	Approved
0.8829	High Similarity	NPD8130	Phase 1
0.8818	High Similarity	NPD6372	Approved
0.8818	High Similarity	NPD6373	Approved
0.8807	High Similarity	NPD5697	Approved
0.875	High Similarity	NPD6882	Approved
0.8739	High Similarity	NPD6883	Approved
0.8739	High Similarity	NPD7102	Approved
0.8739	High Similarity	NPD7290	Approved
0.8716	High Similarity	NPD5739	Approved
0.8716	High Similarity	NPD6675	Approved
0.8716	High Similarity	NPD7128	Approved
0.8716	High Similarity	NPD6402	Approved
0.8661	High Similarity	NPD6869	Approved
0.8661	High Similarity	NPD6617	Approved
0.8661	High Similarity	NPD6847	Approved
0.8649	High Similarity	NPD6013	Approved
0.8649	High Similarity	NPD6014	Approved
0.8649	High Similarity	NPD6012	Approved
0.8611	High Similarity	NPD5211	Phase 2
0.8559	High Similarity	NPD7320	Approved
0.8559	High Similarity	NPD6011	Approved
0.8468	Intermediate Similarity	NPD5701	Approved
0.8455	Intermediate Similarity	NPD5141	Approved
0.8448	Intermediate Similarity	NPD7115	Discovery
0.8426	Intermediate Similarity	NPD5286	Approved
0.8426	Intermediate Similarity	NPD5285	Approved
0.8426	Intermediate Similarity	NPD4696	Approved
0.839	Intermediate Similarity	NPD6319	Approved
0.8348	Intermediate Similarity	NPD4632	Approved
0.8273	Intermediate Similarity	NPD5226	Approved
0.8273	Intermediate Similarity	NPD5224	Approved
0.8273	Intermediate Similarity	NPD5225	Approved
0.8273	Intermediate Similarity	NPD4633	Approved
0.8241	Intermediate Similarity	NPD4755	Approved
0.8241	Intermediate Similarity	NPD6084	Phase 2
0.8241	Intermediate Similarity	NPD6083	Phase 2
0.8198	Intermediate Similarity	NPD5174	Approved
0.8198	Intermediate Similarity	NPD5175	Approved
0.8182	Intermediate Similarity	NPD5223	Approved
0.8174	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD7100	Approved
0.8151	Intermediate Similarity	NPD7101	Approved
0.8091	Intermediate Similarity	NPD4700	Approved
0.8087	Intermediate Similarity	NPD4634	Approved
0.807	Intermediate Similarity	NPD4730	Approved
0.807	Intermediate Similarity	NPD4729	Approved
0.8067	Intermediate Similarity	NPD6335	Approved
0.8051	Intermediate Similarity	NPD6274	Approved
0.8	Intermediate Similarity	NPD5696	Approved
0.7983	Intermediate Similarity	NPD6317	Approved
0.7983	Intermediate Similarity	NPD6009	Approved
0.7982	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD5221	Approved
0.7982	Intermediate Similarity	NPD5222	Approved
0.7967	Intermediate Similarity	NPD7492	Approved
0.7944	Intermediate Similarity	NPD6079	Approved
0.7934	Intermediate Similarity	NPD6054	Approved
0.7931	Intermediate Similarity	NPD5250	Approved
0.7931	Intermediate Similarity	NPD5251	Approved
0.7931	Intermediate Similarity	NPD5249	Phase 3
0.7931	Intermediate Similarity	NPD5248	Approved
0.7931	Intermediate Similarity	NPD5247	Approved
0.792	Intermediate Similarity	NPD7736	Approved
0.7917	Intermediate Similarity	NPD6314	Approved
0.7917	Intermediate Similarity	NPD6313	Approved
0.7909	Intermediate Similarity	NPD5173	Approved
0.7903	Intermediate Similarity	NPD6616	Approved
0.7895	Intermediate Similarity	NPD4768	Approved
0.7895	Intermediate Similarity	NPD4767	Approved
0.789	Intermediate Similarity	NPD5210	Approved
0.789	Intermediate Similarity	NPD5695	Phase 3
0.789	Intermediate Similarity	NPD4629	Approved
0.7886	Intermediate Similarity	NPD7604	Phase 2
0.7869	Intermediate Similarity	NPD5983	Phase 2
0.7869	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7078	Approved
0.7818	Intermediate Similarity	NPD4697	Phase 3
0.7805	Intermediate Similarity	NPD6370	Approved
0.776	Intermediate Similarity	NPD6336	Discontinued
0.7759	Intermediate Similarity	NPD5128	Approved
0.7757	Intermediate Similarity	NPD4753	Phase 2
0.7757	Intermediate Similarity	NPD5328	Approved
0.775	Intermediate Similarity	NPD6868	Approved
0.7739	Intermediate Similarity	NPD6008	Approved
0.7724	Intermediate Similarity	NPD6016	Approved
0.7724	Intermediate Similarity	NPD6015	Approved
0.7724	Intermediate Similarity	NPD6909	Approved
0.7724	Intermediate Similarity	NPD6908	Approved
0.7719	Intermediate Similarity	NPD4754	Approved
0.7712	Intermediate Similarity	NPD5216	Approved
0.7712	Intermediate Similarity	NPD5215	Approved
0.7712	Intermediate Similarity	NPD5217	Approved
0.7706	Intermediate Similarity	NPD6399	Phase 3
0.7698	Intermediate Similarity	NPD8293	Discontinued
0.7661	Intermediate Similarity	NPD5988	Approved
0.7642	Intermediate Similarity	NPD6059	Approved
0.7627	Intermediate Similarity	NPD5135	Approved
0.7627	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5169	Approved
0.7619	Intermediate Similarity	NPD7507	Approved
0.7611	Intermediate Similarity	NPD7640	Approved
0.7611	Intermediate Similarity	NPD7639	Approved
0.7593	Intermediate Similarity	NPD6904	Approved
0.7593	Intermediate Similarity	NPD6080	Approved
0.7593	Intermediate Similarity	NPD6673	Approved
0.7568	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD5127	Approved
0.7545	Intermediate Similarity	NPD4202	Approved
0.7522	Intermediate Similarity	NPD7638	Approved
0.7522	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD6672	Approved
0.75	Intermediate Similarity	NPD5737	Approved
0.7477	Intermediate Similarity	NPD7146	Approved
0.7477	Intermediate Similarity	NPD7521	Approved
0.7477	Intermediate Similarity	NPD7334	Approved
0.7477	Intermediate Similarity	NPD7748	Approved
0.7477	Intermediate Similarity	NPD6409	Approved
0.7477	Intermediate Similarity	NPD3618	Phase 1
0.7477	Intermediate Similarity	NPD6684	Approved
0.7477	Intermediate Similarity	NPD5330	Approved
0.7455	Intermediate Similarity	NPD5693	Phase 1
0.7442	Intermediate Similarity	NPD7319	Approved
0.7434	Intermediate Similarity	NPD7902	Approved
0.7383	Intermediate Similarity	NPD5329	Approved
0.7377	Intermediate Similarity	NPD5167	Approved
0.7339	Intermediate Similarity	NPD6903	Approved
0.7339	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD8328	Phase 3
0.7315	Intermediate Similarity	NPD5690	Phase 2
0.7315	Intermediate Similarity	NPD6098	Approved
0.7311	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5168	Approved
0.7297	Intermediate Similarity	NPD5284	Approved
0.7297	Intermediate Similarity	NPD5281	Approved
0.7297	Intermediate Similarity	NPD5694	Approved
0.7297	Intermediate Similarity	NPD6050	Approved
0.7297	Intermediate Similarity	NPD7515	Phase 2
0.729	Intermediate Similarity	NPD3133	Approved
0.729	Intermediate Similarity	NPD4197	Approved
0.729	Intermediate Similarity	NPD3666	Approved
0.729	Intermediate Similarity	NPD4786	Approved
0.729	Intermediate Similarity	NPD3665	Phase 1
0.7248	Intermediate Similarity	NPD3573	Approved
0.7227	Intermediate Similarity	NPD6412	Phase 2
0.7213	Intermediate Similarity	NPD6053	Discontinued
0.7207	Intermediate Similarity	NPD5692	Phase 3
0.7207	Intermediate Similarity	NPD5785	Approved
0.7168	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6001	Approved
0.7168	Intermediate Similarity	NPD7900	Approved
0.7165	Intermediate Similarity	NPD8033	Approved
0.7165	Intermediate Similarity	NPD7503	Approved
0.7156	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.7107	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3667	Approved
0.7103	Intermediate Similarity	NPD4223	Phase 3
0.7103	Intermediate Similarity	NPD4221	Approved
0.7099	Intermediate Similarity	NPD6033	Approved
0.7087	Intermediate Similarity	NPD8294	Approved
0.7087	Intermediate Similarity	NPD8377	Approved
0.7083	Intermediate Similarity	NPD6614	Approved
0.7064	Intermediate Similarity	NPD5363	Approved
0.7063	Intermediate Similarity	NPD7328	Approved
0.7063	Intermediate Similarity	NPD7327	Approved
0.7054	Intermediate Similarity	NPD5207	Approved
0.7049	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7632	Discontinued
0.7031	Intermediate Similarity	NPD8296	Approved
0.7031	Intermediate Similarity	NPD8379	Approved
0.7031	Intermediate Similarity	NPD8378	Approved
0.7031	Intermediate Similarity	NPD8380	Approved
0.7031	Intermediate Similarity	NPD8335	Approved
0.7027	Intermediate Similarity	NPD5208	Approved
0.7025	Intermediate Similarity	NPD6686	Approved
0.7	Intermediate Similarity	NPD5786	Approved
0.7	Intermediate Similarity	NPD5279	Phase 3
0.7	Intermediate Similarity	NPD5280	Approved
0.7	Intermediate Similarity	NPD4694	Approved
0.6993	Remote Similarity	NPD7236	Approved
0.6991	Remote Similarity	NPD6411	Approved
0.6984	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7260	Phase 2
0.693	Remote Similarity	NPD5778	Approved
0.693	Remote Similarity	NPD5779	Approved
0.6911	Remote Similarity	NPD6371	Approved
0.6909	Remote Similarity	NPD1694	Approved
0.6909	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5091	Approved
0.6881	Remote Similarity	NPD4788	Approved
0.6881	Remote Similarity	NPD5362	Discontinued

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