NPASS Compound

Structure

NPC474315 OpenBabel07101719142D 33 37 0 0 1 0 0 0 0 0999 V2000 2.0074 -2.2294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6180 1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4207 -0.1113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 -1.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3386 -1.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3386 -0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4726 -2.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6720 2.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6666 2.1759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 -0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 -0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6065 1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -2.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 -1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7405 0.6977 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2653 1.3669 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8745 1.1977 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7405 -0.3023 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4726 -0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4726 0.6977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6065 -1.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 0.6977 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6065 -0.8023 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9271 -2.8532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3386 1.1977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 -2.3023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 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 5 6 1 0 0 0 0 5 7 2 0 0 0 0 6 22 2 0 0 0 0 7 25 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 27 1 0 0 0 0 12 15 1 0 0 0 0 12 24 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 29 1 0 0 0 0 15 18 2 0 0 0 0 16 2 1 1 0 0 0 16 19 1 0 0 0 0 17 13 1 6 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 1 0 0 0 20 27 1 1 0 0 0 21 28 1 1 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 30 1 1 0 0 0 24 16 1 1 0 0 0 24 33 1 0 0 0 0 25 28 1 0 0 0 0 25 31 2 0 0 0 0 26 32 2 0 0 0 0 26 33 1 0 0 0 0 27 3 1 1 0 0 0 28 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.27
Volume:	480.831
LogP:	4.028
LogD:	3.69
LogS:	-4.757
# Rotatable Bonds:	3
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.632
Synthetic Accessibility Score:	5.019
Fsp3:	0.75
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:	-4.977
MDCK Permeability:	2.642675281094853e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.231
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.799
30% Bioavailability (F30%):	0.814

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.389
Plasma Protein Binding (PPB):	85.23992156982422%
Volume Distribution (VD):	0.518
Pgp-substrate:	3.8056564331054688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.548
CYP2C19-inhibitor:	0.611
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.593
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.805

ADMET: Excretion

Clearance (CL):	14.868
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.288
Human Hepatotoxicity (H-HT):	0.414
Drug-inuced Liver Injury (DILI):	0.515
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.294
Maximum Recommended Daily Dose:	0.853
Skin Sensitization:	0.942
Carcinogencity:	0.719
Eye Corrosion:	0.015
Eye Irritation:	0.054
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC474315

Natural Product ID:	NPC474315
*Common Name:**	Jaborosalactone B
IUPAC Name:	(2R)-2-[(1S)-1-[(6R,8S,9S,10R,13S,14S,17R)-6-hydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
Synonyms:
Standard InCHIKey:	DZSFTVFZQVZQIU-ZRONUGQKSA-N
Standard InCHI:	InChI=1S/C28H38O5/c1-15-12-24(33-26(32)18(15)14-29)16(2)19-8-9-20-17-13-23(30)22-6-5-7-25(31)28(22,4)21(17)10-11-27(19,20)3/h5-7,16-17,19-21,23-24,29-30H,8-14H2,1-4H3/t16-,17-,19+,20-,21-,23+,24+,27+,28+/m0/s1
SMILES:	CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC(C5=CC=CC(=O)C45C)O)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465076
PubChem CID:	268946
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
NPO18304	Jaborosa integrifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO18304	Jaborosa integrifolia	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	1
Others	5

Activity Type	# Activity
Individual Protein	2
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CQ	=	1.43	uM	PMID[515598]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	3.48	uM	PMID[515598]
NPT2	Others	Unspecified		Ratio	=	11.1	n.a.	PMID[515598]
NPT27	Others	Unspecified		IC50	=	38500.0	nM	PMID[515598]
NPT2	Others	Unspecified		Ratio	=	26.9	n.a.	PMID[515598]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Inhibition	=	19.0	%	PMID[515599]

☑ 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 NPC474315 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	202
0.1-0.2	994
0.2-0.3	3326
0.3-0.4	6956
0.4-0.5	13481
0.5-0.6	7682
0.6-0.7	6678
0.7-0.8	2997
0.8-0.85	302
0.85-0.9	68
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9434	High Similarity	NPC122056
0.9417	High Similarity	NPC91034
0.9346	High Similarity	NPC147912
0.9346	High Similarity	NPC67259
0.9327	High Similarity	NPC220155
0.9174	High Similarity	NPC20302
0.9174	High Similarity	NPC286528
0.9174	High Similarity	NPC140055
0.9174	High Similarity	NPC167606
0.9091	High Similarity	NPC50774
0.9091	High Similarity	NPC709
0.9009	High Similarity	NPC264954
0.9	High Similarity	NPC470492
0.9	High Similarity	NPC312824
0.9	High Similarity	NPC470493
0.9	High Similarity	NPC243065
0.9	High Similarity	NPC183580
0.8981	High Similarity	NPC69291
0.8952	High Similarity	NPC189863
0.8952	High Similarity	NPC266570
0.8929	High Similarity	NPC476962
0.8929	High Similarity	NPC474370
0.885	High Similarity	NPC67569
0.8846	High Similarity	NPC155332
0.8846	High Similarity	NPC114540
0.8846	High Similarity	NPC32577
0.8807	High Similarity	NPC191620
0.8796	High Similarity	NPC29133
0.8772	High Similarity	NPC88326
0.8772	High Similarity	NPC153700
0.8772	High Similarity	NPC470265
0.8772	High Similarity	NPC23786
0.8762	High Similarity	NPC329345
0.8762	High Similarity	NPC473283
0.8762	High Similarity	NPC475526
0.8762	High Similarity	NPC72151
0.875	High Similarity	NPC115899
0.875	High Similarity	NPC282524
0.8739	High Similarity	NPC64318
0.8738	High Similarity	NPC108368
0.8738	High Similarity	NPC57079
0.8716	High Similarity	NPC470961
0.8704	High Similarity	NPC475065
0.8696	High Similarity	NPC469789
0.8692	High Similarity	NPC330011
0.8692	High Similarity	NPC329048
0.8692	High Similarity	NPC473284
0.8673	High Similarity	NPC473274
0.8673	High Similarity	NPC473270
0.8667	High Similarity	NPC320447
0.8661	High Similarity	NPC470959
0.8661	High Similarity	NPC476965
0.8654	High Similarity	NPC474012
0.8654	High Similarity	NPC476299
0.8654	High Similarity	NPC266955
0.8641	High Similarity	NPC2049
0.8641	High Similarity	NPC253826
0.8624	High Similarity	NPC37116
0.8621	High Similarity	NPC8369
0.8621	High Similarity	NPC470494
0.8621	High Similarity	NPC3381
0.8621	High Similarity	NPC8374
0.8611	High Similarity	NPC475418
0.8611	High Similarity	NPC318363
0.8611	High Similarity	NPC473482
0.8585	High Similarity	NPC475050
0.8584	High Similarity	NPC186525
0.8571	High Similarity	NPC476240
0.8571	High Similarity	NPC224720
0.8571	High Similarity	NPC244456
0.8571	High Similarity	NPC270929
0.8571	High Similarity	NPC469657
0.8571	High Similarity	NPC476223
0.8558	High Similarity	NPC478056
0.8558	High Similarity	NPC98868
0.8547	High Similarity	NPC293112
0.8544	High Similarity	NPC471153
0.8544	High Similarity	NPC301534
0.8544	High Similarity	NPC250757
0.8534	High Similarity	NPC11895
0.8522	High Similarity	NPC473256
0.8522	High Similarity	NPC470878
0.8519	High Similarity	NPC475294
0.8509	High Similarity	NPC476960
0.8505	High Similarity	NPC472868
0.8496	Intermediate Similarity	NPC239273
0.8496	Intermediate Similarity	NPC476959
0.8491	Intermediate Similarity	NPC136289
0.8476	Intermediate Similarity	NPC35751
0.8476	Intermediate Similarity	NPC476274
0.8475	Intermediate Similarity	NPC156797
0.8468	Intermediate Similarity	NPC475524
0.8468	Intermediate Similarity	NPC100267
0.8468	Intermediate Similarity	NPC236217
0.8462	Intermediate Similarity	NPC81736
0.8462	Intermediate Similarity	NPC172154
0.8462	Intermediate Similarity	NPC202705
0.8462	Intermediate Similarity	NPC110937
0.8455	Intermediate Similarity	NPC16270
0.8448	Intermediate Similarity	NPC170538
0.8447	Intermediate Similarity	NPC209355
0.8447	Intermediate Similarity	NPC88310
0.8435	Intermediate Similarity	NPC476961
0.8421	Intermediate Similarity	NPC146786
0.8421	Intermediate Similarity	NPC329736
0.8411	Intermediate Similarity	NPC95899
0.8411	Intermediate Similarity	NPC112009
0.8411	Intermediate Similarity	NPC476237
0.8411	Intermediate Similarity	NPC476889
0.8407	Intermediate Similarity	NPC148458
0.8407	Intermediate Similarity	NPC476963
0.8396	Intermediate Similarity	NPC310981
0.8396	Intermediate Similarity	NPC81530
0.8396	Intermediate Similarity	NPC168319
0.8396	Intermediate Similarity	NPC194028
0.8396	Intermediate Similarity	NPC99411
0.8393	Intermediate Similarity	NPC25909
0.8381	Intermediate Similarity	NPC316598
0.8381	Intermediate Similarity	NPC235464
0.8381	Intermediate Similarity	NPC166745
0.8381	Intermediate Similarity	NPC103051
0.8378	Intermediate Similarity	NPC470960
0.8376	Intermediate Similarity	NPC204812
0.8365	Intermediate Similarity	NPC242848
0.8364	Intermediate Similarity	NPC137911
0.8364	Intermediate Similarity	NPC228477
0.8362	Intermediate Similarity	NPC46570
0.835	Intermediate Similarity	NPC474690
0.8348	Intermediate Similarity	NPC61520
0.8333	Intermediate Similarity	NPC221414
0.8333	Intermediate Similarity	NPC473593
0.8319	Intermediate Similarity	NPC474181
0.8319	Intermediate Similarity	NPC470953
0.8319	Intermediate Similarity	NPC284915
0.8318	Intermediate Similarity	NPC31058
0.8318	Intermediate Similarity	NPC40918
0.8318	Intermediate Similarity	NPC469606
0.8318	Intermediate Similarity	NPC273005
0.8318	Intermediate Similarity	NPC476890
0.8305	Intermediate Similarity	NPC241456
0.8305	Intermediate Similarity	NPC32868
0.8304	Intermediate Similarity	NPC285956
0.8304	Intermediate Similarity	NPC476163
0.8304	Intermediate Similarity	NPC475970
0.8302	Intermediate Similarity	NPC201406
0.8291	Intermediate Similarity	NPC107493
0.8291	Intermediate Similarity	NPC269642
0.8288	Intermediate Similarity	NPC473627
0.8286	Intermediate Similarity	NPC141401
0.8286	Intermediate Similarity	NPC156546
0.8286	Intermediate Similarity	NPC474343
0.8286	Intermediate Similarity	NPC108078
0.8276	Intermediate Similarity	NPC184555
0.8273	Intermediate Similarity	NPC472825
0.8269	Intermediate Similarity	NPC180950
0.8269	Intermediate Similarity	NPC33473
0.8269	Intermediate Similarity	NPC171395
0.8261	Intermediate Similarity	NPC311554
0.8261	Intermediate Similarity	NPC257457
0.8252	Intermediate Similarity	NPC115021
0.8241	Intermediate Similarity	NPC180204
0.8241	Intermediate Similarity	NPC297617
0.8241	Intermediate Similarity	NPC478057
0.8235	Intermediate Similarity	NPC273199
0.8235	Intermediate Similarity	NPC473635
0.823	Intermediate Similarity	NPC472929
0.823	Intermediate Similarity	NPC73050
0.8224	Intermediate Similarity	NPC476888
0.8224	Intermediate Similarity	NPC472637
0.8224	Intermediate Similarity	NPC93744
0.8224	Intermediate Similarity	NPC473514
0.822	Intermediate Similarity	NPC55602
0.8208	Intermediate Similarity	NPC92275
0.8198	Intermediate Similarity	NPC75389
0.8197	Intermediate Similarity	NPC231240
0.819	Intermediate Similarity	NPC78473
0.819	Intermediate Similarity	NPC122324
0.819	Intermediate Similarity	NPC151725
0.819	Intermediate Similarity	NPC475041
0.819	Intermediate Similarity	NPC29152
0.819	Intermediate Similarity	NPC106425
0.819	Intermediate Similarity	NPC475520
0.819	Intermediate Similarity	NPC190713
0.8182	Intermediate Similarity	NPC476966
0.8182	Intermediate Similarity	NPC472925
0.8182	Intermediate Similarity	NPC476958
0.8174	Intermediate Similarity	NPC55296
0.8174	Intermediate Similarity	NPC471854
0.8174	Intermediate Similarity	NPC472934
0.8174	Intermediate Similarity	NPC474518
0.8173	Intermediate Similarity	NPC299100
0.8173	Intermediate Similarity	NPC473431
0.8173	Intermediate Similarity	NPC471078
0.8173	Intermediate Similarity	NPC473280
0.8173	Intermediate Similarity	NPC469406
0.8173	Intermediate Similarity	NPC8993
0.8173	Intermediate Similarity	NPC473435
0.8173	Intermediate Similarity	NPC53685
0.8173	Intermediate Similarity	NPC470697
0.8165	Intermediate Similarity	NPC189616

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 NPC474315 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1147
0.2-0.3	3188
0.3-0.4	2910
0.4-0.5	1092
0.5-0.6	293
0.6-0.7	205
0.7-0.8	141
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9174	High Similarity	NPD7115	Discovery
0.8077	Intermediate Similarity	NPD6399	Phase 3
0.8037	Intermediate Similarity	NPD4225	Approved
0.7963	Intermediate Similarity	NPD7640	Approved
0.7963	Intermediate Similarity	NPD7639	Approved
0.7946	Intermediate Similarity	NPD6881	Approved
0.7946	Intermediate Similarity	NPD6899	Approved
0.7895	Intermediate Similarity	NPD6650	Approved
0.7895	Intermediate Similarity	NPD6649	Approved
0.7885	Intermediate Similarity	NPD5785	Approved
0.787	Intermediate Similarity	NPD7638	Approved
0.7857	Intermediate Similarity	NPD5697	Approved
0.781	Intermediate Similarity	NPD6079	Approved
0.781	Intermediate Similarity	NPD7637	Suspended
0.7807	Intermediate Similarity	NPD7290	Approved
0.7807	Intermediate Similarity	NPD6883	Approved
0.7807	Intermediate Similarity	NPD7102	Approved
0.7778	Intermediate Similarity	NPD6083	Phase 2
0.7778	Intermediate Similarity	NPD6084	Phase 2
0.7768	Intermediate Similarity	NPD5739	Approved
0.7768	Intermediate Similarity	NPD6675	Approved
0.7768	Intermediate Similarity	NPD6402	Approved
0.7768	Intermediate Similarity	NPD7128	Approved
0.7739	Intermediate Similarity	NPD6847	Approved
0.7739	Intermediate Similarity	NPD8130	Phase 1
0.7739	Intermediate Similarity	NPD6617	Approved
0.7739	Intermediate Similarity	NPD6869	Approved
0.7719	Intermediate Similarity	NPD6012	Approved
0.7719	Intermediate Similarity	NPD6372	Approved
0.7719	Intermediate Similarity	NPD6014	Approved
0.7719	Intermediate Similarity	NPD6013	Approved
0.7719	Intermediate Similarity	NPD6373	Approved
0.7672	Intermediate Similarity	NPD6882	Approved
0.7672	Intermediate Similarity	NPD8297	Approved
0.767	Intermediate Similarity	NPD3618	Phase 1
0.7664	Intermediate Similarity	NPD7748	Approved
0.7658	Intermediate Similarity	NPD5211	Phase 2
0.7647	Intermediate Similarity	NPD4786	Approved
0.7642	Intermediate Similarity	NPD6411	Approved
0.7642	Intermediate Similarity	NPD7515	Phase 2
0.7632	Intermediate Similarity	NPD6011	Approved
0.7632	Intermediate Similarity	NPD7320	Approved
0.7619	Intermediate Similarity	NPD5328	Approved
0.7615	Intermediate Similarity	NPD7902	Approved
0.757	Intermediate Similarity	NPD5779	Approved
0.757	Intermediate Similarity	NPD5778	Approved
0.7545	Intermediate Similarity	NPD5696	Approved
0.7544	Intermediate Similarity	NPD5701	Approved
0.7524	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD6672	Approved
0.7524	Intermediate Similarity	NPD5737	Approved
0.7523	Intermediate Similarity	NPD5221	Approved
0.7523	Intermediate Similarity	NPD5222	Approved
0.7523	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD5141	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.7477	Intermediate Similarity	NPD5281	Approved
0.7477	Intermediate Similarity	NPD5284	Approved
0.7477	Intermediate Similarity	NPD5285	Approved
0.7477	Intermediate Similarity	NPD5286	Approved
0.7477	Intermediate Similarity	NPD4696	Approved
0.7455	Intermediate Similarity	NPD5173	Approved
0.7453	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6101	Approved
0.7451	Intermediate Similarity	NPD3667	Approved
0.7431	Intermediate Similarity	NPD4629	Approved
0.7431	Intermediate Similarity	NPD5695	Phase 3
0.7431	Intermediate Similarity	NPD5210	Approved
0.7404	Intermediate Similarity	NPD5363	Approved
0.7404	Intermediate Similarity	NPD1694	Approved
0.7377	Intermediate Similarity	NPD6319	Approved
0.7364	Intermediate Similarity	NPD4697	Phase 3
0.7358	Intermediate Similarity	NPD6903	Approved
0.7345	Intermediate Similarity	NPD4633	Approved
0.7345	Intermediate Similarity	NPD5226	Approved
0.7345	Intermediate Similarity	NPD7632	Discontinued
0.7345	Intermediate Similarity	NPD5224	Approved
0.7345	Intermediate Similarity	NPD5225	Approved
0.7339	Intermediate Similarity	NPD7900	Approved
0.7339	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5279	Phase 3
0.7333	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6868	Approved
0.7317	Intermediate Similarity	NPD7503	Approved
0.7315	Intermediate Similarity	NPD8034	Phase 2
0.7315	Intermediate Similarity	NPD5693	Phase 1
0.7315	Intermediate Similarity	NPD8035	Phase 2
0.7308	Intermediate Similarity	NPD3666	Approved
0.7308	Intermediate Similarity	NPD3133	Approved
0.7308	Intermediate Similarity	NPD3665	Phase 1
0.7297	Intermediate Similarity	NPD4755	Approved
0.7295	Intermediate Similarity	NPD7100	Approved
0.7295	Intermediate Similarity	NPD7101	Approved
0.729	Intermediate Similarity	NPD4753	Phase 2
0.7288	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5175	Approved
0.7281	Intermediate Similarity	NPD5174	Approved
0.728	Intermediate Similarity	NPD7492	Approved
0.7273	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5223	Approved
0.7248	Intermediate Similarity	NPD4202	Approved
0.7244	Intermediate Similarity	NPD7736	Approved
0.7238	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6054	Approved
0.7227	Intermediate Similarity	NPD6053	Discontinued
0.7222	Intermediate Similarity	NPD5207	Approved
0.7222	Intermediate Similarity	NPD6616	Approved
0.7213	Intermediate Similarity	NPD6335	Approved
0.7203	Intermediate Similarity	NPD4634	Approved
0.719	Intermediate Similarity	NPD6274	Approved
0.7188	Intermediate Similarity	NPD7319	Approved
0.7179	Intermediate Similarity	NPD6686	Approved
0.7168	Intermediate Similarity	NPD4700	Approved
0.7167	Intermediate Similarity	NPD4632	Approved
0.7165	Intermediate Similarity	NPD7078	Approved
0.7156	Intermediate Similarity	NPD6050	Approved
0.7156	Intermediate Similarity	NPD5694	Approved
0.7155	Intermediate Similarity	NPD6008	Approved
0.7131	Intermediate Similarity	NPD6317	Approved
0.713	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6673	Approved
0.713	Intermediate Similarity	NPD6904	Approved
0.713	Intermediate Similarity	NPD6080	Approved
0.712	Intermediate Similarity	NPD6370	Approved
0.7115	Intermediate Similarity	NPD4269	Approved
0.7115	Intermediate Similarity	NPD4270	Approved
0.7103	Intermediate Similarity	NPD3573	Approved
0.7094	Intermediate Similarity	NPD6412	Phase 2
0.7087	Intermediate Similarity	NPD7507	Approved
0.7073	Intermediate Similarity	NPD6314	Approved
0.7073	Intermediate Similarity	NPD6313	Approved
0.7064	Intermediate Similarity	NPD5692	Phase 3
0.7059	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6371	Approved
0.704	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD8513	Phase 3
0.704	Intermediate Similarity	NPD6015	Approved
0.704	Intermediate Similarity	NPD6016	Approved
0.7034	Intermediate Similarity	NPD4729	Approved
0.7034	Intermediate Similarity	NPD4730	Approved
0.7018	Intermediate Similarity	NPD6404	Discontinued
0.7009	Intermediate Similarity	NPD5786	Approved
0.6992	Remote Similarity	NPD6009	Approved
0.6984	Remote Similarity	NPD5988	Approved
0.6981	Remote Similarity	NPD3668	Phase 3
0.6975	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6051	Approved
0.696	Remote Similarity	NPD6059	Approved
0.6952	Remote Similarity	NPD4223	Phase 3
0.6952	Remote Similarity	NPD4221	Approved
0.6929	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD4252	Approved
0.6917	Remote Similarity	NPD5247	Approved
0.6917	Remote Similarity	NPD5249	Phase 3
0.6917	Remote Similarity	NPD5250	Approved
0.6917	Remote Similarity	NPD5248	Approved
0.6917	Remote Similarity	NPD5251	Approved
0.6917	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5329	Approved
0.6905	Remote Similarity	NPD6908	Approved
0.6905	Remote Similarity	NPD8516	Approved
0.6905	Remote Similarity	NPD6909	Approved
0.6905	Remote Similarity	NPD8515	Approved
0.6905	Remote Similarity	NPD8517	Approved
0.6905	Remote Similarity	NPD5983	Phase 2
0.6899	Remote Similarity	NPD8293	Discontinued
0.6891	Remote Similarity	NPD5128	Approved
0.6891	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5168	Approved
0.6887	Remote Similarity	NPD5362	Discontinued
0.6887	Remote Similarity	NPD6695	Phase 3
0.6881	Remote Similarity	NPD5208	Approved
0.6879	Remote Similarity	NPD7236	Approved
0.6875	Remote Similarity	NPD6001	Approved
0.6864	Remote Similarity	NPD4767	Approved
0.6864	Remote Similarity	NPD4768	Approved
0.686	Remote Similarity	NPD5217	Approved
0.686	Remote Similarity	NPD5215	Approved
0.686	Remote Similarity	NPD5216	Approved
0.6857	Remote Similarity	NPD5369	Approved
0.6852	Remote Similarity	NPD4519	Discontinued
0.6852	Remote Similarity	NPD6098	Approved
0.6852	Remote Similarity	NPD5280	Approved
0.6852	Remote Similarity	NPD4623	Approved
0.6852	Remote Similarity	NPD4694	Approved
0.6852	Remote Similarity	NPD5690	Phase 2
0.6838	Remote Similarity	NPD4754	Approved
0.6822	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4197	Approved
0.6822	Remote Similarity	NPD6336	Discontinued
0.6818	Remote Similarity	NPD7260	Phase 2
0.68	Remote Similarity	NPD7328	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