NPASS Compound

Structure

NPC255021 OpenBabel07101718202D 31 35 0 0 1 0 0 0 0 0999 V2000 6.4325 5.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6915 1.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1453 3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 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 0.8660 1.5000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7436 3.0748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1235 4.1270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8581 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0005 2.4057 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7926 3.3838 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 23 1 0 0 0 0 9 24 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 29 1 0 0 0 0 13 28 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 15 26 2 0 0 0 0 16 27 1 0 0 0 0 17 1 1 1 0 0 0 18 2 1 6 0 0 0 18 23 1 0 0 0 0 19 3 1 1 0 0 0 19 21 1 0 0 0 0 20 30 2 0 0 0 0 21 17 1 6 0 0 0 22 16 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 28 1 1 0 0 0 24 28 1 1 0 0 0 25 29 1 1 0 0 0 26 27 1 0 0 0 0 26 29 1 0 0 0 0 27 31 2 0 0 0 0 28 4 1 1 0 0 0 29 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.33
Volume:	477.029
LogP:	5.546
LogD:	5.98
LogS:	-5.219
# Rotatable Bonds:	5
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.439
Synthetic Accessibility Score:	4.973
Fsp3:	0.862
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.006
MDCK Permeability:	1.3182506336306687e-05
Pgp-inhibitor:	0.928
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.65
Plasma Protein Binding (PPB):	94.19884490966797%
Volume Distribution (VD):	1.368
Pgp-substrate:	1.2211891412734985%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.641
CYP2C19-inhibitor:	0.155
CYP2C19-substrate:	0.948
CYP2C9-inhibitor:	0.19
CYP2C9-substrate:	0.523
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.647
CYP3A4-substrate:	0.791

ADMET: Excretion

Clearance (CL):	7.197
Half-life (T1/2):	0.336

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.591
Drug-inuced Liver Injury (DILI):	0.78
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.14
Maximum Recommended Daily Dose:	0.162
Skin Sensitization:	0.73
Carcinogencity:	0.038
Eye Corrosion:	0.173
Eye Irritation:	0.147
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC255021

Natural Product ID:	NPC255021
*Common Name:**	Petrosterol-3,6-Dione
IUPAC Name:	(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R,5R)-5-[(1R,2R)-2-methylcyclopropyl]hexan-2-yl]-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,6-dione
Synonyms:	Petrosterol-3,6-Dione
Standard InCHIKey:	PEVBPRIVSRIENZ-CAIFUOAHSA-N
Standard InCHI:	InChI=1S/C29H44O2/c1-17(21-14-19(21)3)6-7-18(2)23-8-9-24-22-16-27(31)26-15-20(30)10-12-29(26,5)25(22)11-13-28(23,24)4/h15,17-19,21-25H,6-14,16H2,1-5H3/t17-,18-,19-,21+,22+,23-,24+,25+,28-,29-/m1/s1
SMILES:	O=C1CC[C@]2(C(=C1)C(=O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CC[C@H]([C@@H]1C[C@H]1C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550118
PubChem CID:	45271863
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols 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
NPO32556	Ianthella sp.	Species	Thorectidae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[19615900]
NPO32556	Ianthella sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8254355]

☑ 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	6
Others	3

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	48.83	%	PMID[573736]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	21.85	%	PMID[573736]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	11.19	%	PMID[573736]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	22100.0	nM	PMID[573736]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	16200.0	nM	PMID[573736]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	17800.0	nM	PMID[573736]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	48200.0	nM	PMID[573736]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	19900.0	nM	PMID[573736]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8400.0	nM	PMID[573736]

☑ 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 NPC255021 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	194
0.1-0.2	2318
0.2-0.3	13587
0.3-0.4	11672
0.4-0.5	7763
0.5-0.6	5003
0.6-0.7	1736
0.7-0.8	354
0.8-0.85	39
0.85-0.9	14
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC69408
0.9565	High Similarity	NPC303613
0.9565	High Similarity	NPC474228
0.942	High Similarity	NPC305501
0.9296	High Similarity	NPC255650
0.9286	High Similarity	NPC251705
0.9275	High Similarity	NPC251929
0.9275	High Similarity	NPC265782
0.9275	High Similarity	NPC2634
0.9275	High Similarity	NPC35734
0.9275	High Similarity	NPC159577
0.9275	High Similarity	NPC307176
0.9275	High Similarity	NPC282593
0.9155	High Similarity	NPC309852
0.9143	High Similarity	NPC54123
0.9143	High Similarity	NPC115023
0.9143	High Similarity	NPC5701
0.9143	High Similarity	NPC234707
0.913	High Similarity	NPC139397
0.9028	High Similarity	NPC293803
0.9014	High Similarity	NPC470045
0.9014	High Similarity	NPC470044
0.9	High Similarity	NPC260040
0.9	High Similarity	NPC477856
0.9	High Similarity	NPC214770
0.8986	High Similarity	NPC20610
0.8857	High Similarity	NPC477857
0.8857	High Similarity	NPC182815
0.8684	High Similarity	NPC474509
0.863	High Similarity	NPC329866
0.863	High Similarity	NPC474796
0.863	High Similarity	NPC474797
0.8611	High Similarity	NPC223187
0.8611	High Similarity	NPC470078
0.8571	High Similarity	NPC176107
0.8553	High Similarity	NPC170793
0.8553	High Similarity	NPC90965
0.8514	High Similarity	NPC473171
0.8481	Intermediate Similarity	NPC178025
0.8481	Intermediate Similarity	NPC181743
0.8481	Intermediate Similarity	NPC16287
0.8472	Intermediate Similarity	NPC40574
0.8462	Intermediate Similarity	NPC472239
0.8451	Intermediate Similarity	NPC260474
0.8451	Intermediate Similarity	NPC188292
0.8429	Intermediate Similarity	NPC323005
0.8429	Intermediate Similarity	NPC189917
0.8429	Intermediate Similarity	NPC107704
0.8429	Intermediate Similarity	NPC39462
0.8429	Intermediate Similarity	NPC96812
0.8429	Intermediate Similarity	NPC92327
0.8429	Intermediate Similarity	NPC168824
0.8406	Intermediate Similarity	NPC212210
0.8406	Intermediate Similarity	NPC285371
0.8375	Intermediate Similarity	NPC60350
0.8356	Intermediate Similarity	NPC190035
0.8333	Intermediate Similarity	NPC256846
0.8261	Intermediate Similarity	NPC165695
0.8228	Intermediate Similarity	NPC142253
0.8228	Intermediate Similarity	NPC472867
0.8228	Intermediate Similarity	NPC100297
0.8228	Intermediate Similarity	NPC320514
0.8228	Intermediate Similarity	NPC3511
0.8194	Intermediate Similarity	NPC310992
0.8194	Intermediate Similarity	NPC87141
0.8182	Intermediate Similarity	NPC469996
0.8182	Intermediate Similarity	NPC470052
0.8182	Intermediate Similarity	NPC82635
0.8171	Intermediate Similarity	NPC476293
0.8158	Intermediate Similarity	NPC469793
0.8158	Intermediate Similarity	NPC474463
0.8158	Intermediate Similarity	NPC469796
0.8148	Intermediate Similarity	NPC29447
0.8143	Intermediate Similarity	NPC469662
0.8116	Intermediate Similarity	NPC213152
0.8108	Intermediate Similarity	NPC181204
0.8108	Intermediate Similarity	NPC304983
0.8108	Intermediate Similarity	NPC225467
0.8082	Intermediate Similarity	NPC286814
0.8056	Intermediate Similarity	NPC20181
0.8056	Intermediate Similarity	NPC220210
0.8056	Intermediate Similarity	NPC475523
0.8052	Intermediate Similarity	NPC91665
0.8028	Intermediate Similarity	NPC251118
0.8025	Intermediate Similarity	NPC214043
0.8025	Intermediate Similarity	NPC85774
0.8025	Intermediate Similarity	NPC87552
0.8	Intermediate Similarity	NPC202118
0.8	Intermediate Similarity	NPC197238
0.8	Intermediate Similarity	NPC193347
0.8	Intermediate Similarity	NPC472306
0.7975	Intermediate Similarity	NPC472478
0.7973	Intermediate Similarity	NPC151045
0.7973	Intermediate Similarity	NPC246722
0.7971	Intermediate Similarity	NPC127582
0.7971	Intermediate Similarity	NPC25853
0.7952	Intermediate Similarity	NPC93778
0.7949	Intermediate Similarity	NPC115515
0.7949	Intermediate Similarity	NPC228911
0.7945	Intermediate Similarity	NPC82477
0.7945	Intermediate Similarity	NPC39157
0.7945	Intermediate Similarity	NPC296697
0.7945	Intermediate Similarity	NPC142754
0.7945	Intermediate Similarity	NPC155198
0.7927	Intermediate Similarity	NPC469948
0.7927	Intermediate Similarity	NPC8571
0.7917	Intermediate Similarity	NPC176171
0.7917	Intermediate Similarity	NPC43300
0.7901	Intermediate Similarity	NPC41539
0.7895	Intermediate Similarity	NPC211641
0.7895	Intermediate Similarity	NPC128346
0.7895	Intermediate Similarity	NPC219232
0.7895	Intermediate Similarity	NPC159497
0.7887	Intermediate Similarity	NPC475124
0.7875	Intermediate Similarity	NPC147066
0.7875	Intermediate Similarity	NPC477372
0.7857	Intermediate Similarity	NPC60565
0.7848	Intermediate Similarity	NPC190211
0.7848	Intermediate Similarity	NPC215843
0.7831	Intermediate Similarity	NPC474733
0.7831	Intermediate Similarity	NPC145879
0.7831	Intermediate Similarity	NPC31564
0.7831	Intermediate Similarity	NPC474732
0.7831	Intermediate Similarity	NPC474778
0.7826	Intermediate Similarity	NPC259261
0.7826	Intermediate Similarity	NPC276764
0.7826	Intermediate Similarity	NPC472304
0.7821	Intermediate Similarity	NPC470557
0.7805	Intermediate Similarity	NPC237712
0.7805	Intermediate Similarity	NPC473246
0.7805	Intermediate Similarity	NPC144258
0.7794	Intermediate Similarity	NPC192427
0.7791	Intermediate Similarity	NPC23217
0.7778	Intermediate Similarity	NPC470329
0.7778	Intermediate Similarity	NPC469805
0.7778	Intermediate Similarity	NPC327969
0.7778	Intermediate Similarity	NPC469804
0.7778	Intermediate Similarity	NPC321289
0.7765	Intermediate Similarity	NPC262043
0.7763	Intermediate Similarity	NPC52667
0.7763	Intermediate Similarity	NPC474488
0.775	Intermediate Similarity	NPC469798
0.775	Intermediate Similarity	NPC469797
0.7746	Intermediate Similarity	NPC32285
0.7746	Intermediate Similarity	NPC288253
0.7738	Intermediate Similarity	NPC58063
0.7738	Intermediate Similarity	NPC136948
0.7738	Intermediate Similarity	NPC475740
0.7722	Intermediate Similarity	NPC105197
0.7714	Intermediate Similarity	NPC270042
0.7711	Intermediate Similarity	NPC472931
0.7711	Intermediate Similarity	NPC11711
0.7711	Intermediate Similarity	NPC472940
0.7692	Intermediate Similarity	NPC1254
0.7683	Intermediate Similarity	NPC470047
0.7683	Intermediate Similarity	NPC474790
0.7683	Intermediate Similarity	NPC279639
0.7683	Intermediate Similarity	NPC3856
0.7683	Intermediate Similarity	NPC474976
0.7683	Intermediate Similarity	NPC470015
0.7683	Intermediate Similarity	NPC470046
0.7683	Intermediate Similarity	NPC168188
0.7681	Intermediate Similarity	NPC94991
0.7681	Intermediate Similarity	NPC266295
0.7681	Intermediate Similarity	NPC30215
0.7681	Intermediate Similarity	NPC27610
0.7681	Intermediate Similarity	NPC56905
0.7654	Intermediate Similarity	NPC4166
0.7654	Intermediate Similarity	NPC278459
0.7654	Intermediate Similarity	NPC201912
0.7654	Intermediate Similarity	NPC38350
0.7647	Intermediate Similarity	NPC117122
0.7647	Intermediate Similarity	NPC259252
0.7639	Intermediate Similarity	NPC473902
0.7632	Intermediate Similarity	NPC474562
0.7625	Intermediate Similarity	NPC476177
0.7625	Intermediate Similarity	NPC472490
0.7625	Intermediate Similarity	NPC158846
0.7625	Intermediate Similarity	NPC477371
0.7619	Intermediate Similarity	NPC195640
0.7619	Intermediate Similarity	NPC222613
0.7619	Intermediate Similarity	NPC475022
0.7619	Intermediate Similarity	NPC186975
0.7619	Intermediate Similarity	NPC118648
0.7614	Intermediate Similarity	NPC294266
0.7606	Intermediate Similarity	NPC475795
0.7595	Intermediate Similarity	NPC472300
0.759	Intermediate Similarity	NPC227064
0.759	Intermediate Similarity	NPC58841
0.759	Intermediate Similarity	NPC472265
0.759	Intermediate Similarity	NPC161423
0.759	Intermediate Similarity	NPC321187
0.759	Intermediate Similarity	NPC82902
0.759	Intermediate Similarity	NPC329043
0.759	Intermediate Similarity	NPC59453
0.759	Intermediate Similarity	NPC320801
0.759	Intermediate Similarity	NPC221758
0.7586	Intermediate Similarity	NPC218301
0.7586	Intermediate Similarity	NPC272746
0.7568	Intermediate Similarity	NPC4370

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 NPC255021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	2406
0.2-0.3	4602
0.3-0.4	1362
0.4-0.5	271
0.5-0.6	143
0.6-0.7	122
0.7-0.8	57
0.8-0.85	4
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9275	High Similarity	NPD4747	Approved
0.9275	High Similarity	NPD4691	Approved
0.913	High Similarity	NPD4137	Phase 3
0.8889	High Similarity	NPD4058	Approved
0.8889	High Similarity	NPD5733	Approved
0.863	High Similarity	NPD4687	Approved
0.8611	High Similarity	NPD5276	Approved
0.8451	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4221	Approved
0.8	Intermediate Similarity	NPD4223	Phase 3
0.7927	Intermediate Similarity	NPD5329	Approved
0.7805	Intermediate Similarity	NPD4197	Approved
0.7722	Intermediate Similarity	NPD3617	Approved
0.7683	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD8028	Phase 2
0.7647	Intermediate Similarity	NPD6672	Approved
0.7647	Intermediate Similarity	NPD5737	Approved
0.7619	Intermediate Similarity	NPD4690	Approved
0.7619	Intermediate Similarity	NPD5690	Phase 2
0.7619	Intermediate Similarity	NPD6409	Approved
0.7619	Intermediate Similarity	NPD6684	Approved
0.7619	Intermediate Similarity	NPD5205	Approved
0.7619	Intermediate Similarity	NPD5330	Approved
0.7619	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4688	Approved
0.7619	Intermediate Similarity	NPD4138	Approved
0.7619	Intermediate Similarity	NPD7521	Approved
0.7619	Intermediate Similarity	NPD7334	Approved
0.7619	Intermediate Similarity	NPD4689	Approved
0.7619	Intermediate Similarity	NPD7146	Approved
0.7619	Intermediate Similarity	NPD4693	Phase 3
0.759	Intermediate Similarity	NPD3665	Phase 1
0.759	Intermediate Similarity	NPD3666	Approved
0.759	Intermediate Similarity	NPD3133	Approved
0.759	Intermediate Similarity	NPD4786	Approved
0.7586	Intermediate Similarity	NPD6079	Approved
0.7558	Intermediate Similarity	NPD5328	Approved
0.7558	Intermediate Similarity	NPD6904	Approved
0.7558	Intermediate Similarity	NPD6673	Approved
0.7558	Intermediate Similarity	NPD6080	Approved
0.7528	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6903	Approved
0.7442	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5208	Approved
0.7416	Intermediate Similarity	NPD6001	Approved
0.7412	Intermediate Similarity	NPD6098	Approved
0.7412	Intermediate Similarity	NPD3618	Phase 1
0.7412	Intermediate Similarity	NPD4694	Approved
0.7412	Intermediate Similarity	NPD5280	Approved
0.7407	Intermediate Similarity	NPD4195	Approved
0.7356	Intermediate Similarity	NPD4753	Phase 2
0.7349	Intermediate Similarity	NPD3667	Approved
0.7317	Intermediate Similarity	NPD4695	Discontinued
0.7303	Intermediate Similarity	NPD5133	Approved
0.7209	Intermediate Similarity	NPD5279	Phase 3
0.7191	Intermediate Similarity	NPD5693	Phase 1
0.7191	Intermediate Similarity	NPD6050	Approved
0.7183	Intermediate Similarity	NPD287	Approved
0.7176	Intermediate Similarity	NPD3668	Phase 3
0.7143	Intermediate Similarity	NPD4629	Approved
0.7143	Intermediate Similarity	NPD5210	Approved
0.7111	Intermediate Similarity	NPD4202	Approved
0.7079	Intermediate Similarity	NPD5692	Phase 3
0.7079	Intermediate Similarity	NPD5207	Approved
0.7065	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5222	Approved
0.7065	Intermediate Similarity	NPD5221	Approved
0.7059	Intermediate Similarity	NPD4788	Approved
0.7024	Intermediate Similarity	NPD4692	Approved
0.7024	Intermediate Similarity	NPD4139	Approved
0.7011	Intermediate Similarity	NPD4519	Discontinued
0.7011	Intermediate Similarity	NPD4623	Approved
0.7	Intermediate Similarity	NPD5694	Approved
0.7	Intermediate Similarity	NPD5284	Approved
0.7	Intermediate Similarity	NPD5281	Approved
0.6989	Remote Similarity	NPD6083	Phase 2
0.6989	Remote Similarity	NPD6084	Phase 2
0.6989	Remote Similarity	NPD5173	Approved
0.6989	Remote Similarity	NPD5959	Approved
0.6932	Remote Similarity	NPD3573	Approved
0.6923	Remote Similarity	NPD6399	Phase 3
0.6889	Remote Similarity	NPD4096	Approved
0.6882	Remote Similarity	NPD4697	Phase 3
0.6842	Remote Similarity	NPD5285	Approved
0.6842	Remote Similarity	NPD5286	Approved
0.6842	Remote Similarity	NPD4696	Approved
0.6809	Remote Similarity	NPD4755	Approved
0.6778	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5695	Phase 3
0.6774	Remote Similarity	NPD5654	Approved
0.6771	Remote Similarity	NPD5223	Approved
0.675	Remote Similarity	NPD4243	Approved
0.6737	Remote Similarity	NPD5696	Approved
0.6701	Remote Similarity	NPD5226	Approved
0.6701	Remote Similarity	NPD4633	Approved
0.6701	Remote Similarity	NPD5225	Approved
0.6701	Remote Similarity	NPD5224	Approved
0.6701	Remote Similarity	NPD5211	Phase 2
0.6701	Remote Similarity	NPD5091	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD4518	Approved
0.6633	Remote Similarity	NPD5174	Approved
0.6633	Remote Similarity	NPD5175	Approved
0.6633	Remote Similarity	NPD6052	Approved
0.663	Remote Similarity	NPD7515	Phase 2
0.66	Remote Similarity	NPD6614	Approved
0.6585	Remote Similarity	NPD4784	Approved
0.6585	Remote Similarity	NPD4785	Approved
0.6566	Remote Similarity	NPD5141	Approved
0.6552	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6899	Approved
0.6535	Remote Similarity	NPD6881	Approved
0.6526	Remote Similarity	NPD7732	Phase 3
0.6526	Remote Similarity	NPD7614	Phase 1
0.6506	Remote Similarity	NPD6942	Approved
0.6506	Remote Similarity	NPD7339	Approved
0.65	Remote Similarity	NPD6008	Approved
0.65	Remote Similarity	NPD5739	Approved
0.65	Remote Similarity	NPD6402	Approved
0.65	Remote Similarity	NPD7128	Approved
0.65	Remote Similarity	NPD6675	Approved
0.6495	Remote Similarity	NPD6404	Discontinued
0.6489	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7900	Approved
0.6489	Remote Similarity	NPD7748	Approved
0.6489	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4754	Approved
0.6436	Remote Similarity	NPD5697	Approved
0.6408	Remote Similarity	NPD7102	Approved
0.6408	Remote Similarity	NPD6883	Approved
0.6408	Remote Similarity	NPD7290	Approved
0.6375	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD5360	Phase 3
0.6373	Remote Similarity	NPD5128	Approved
0.6373	Remote Similarity	NPD7320	Approved
0.6373	Remote Similarity	NPD5168	Approved
0.6373	Remote Similarity	NPD6011	Approved
0.6373	Remote Similarity	NPD4730	Approved
0.6373	Remote Similarity	NPD4729	Approved
0.6346	Remote Similarity	NPD6847	Approved
0.6346	Remote Similarity	NPD6649	Approved
0.6346	Remote Similarity	NPD6617	Approved
0.6346	Remote Similarity	NPD8130	Phase 1
0.6346	Remote Similarity	NPD6650	Approved
0.6346	Remote Similarity	NPD6869	Approved
0.6337	Remote Similarity	NPD4768	Approved
0.6337	Remote Similarity	NPD4767	Approved
0.6333	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1694	Approved
0.6329	Remote Similarity	NPD7331	Phase 2
0.6311	Remote Similarity	NPD6373	Approved
0.6311	Remote Similarity	NPD6013	Approved
0.6311	Remote Similarity	NPD6372	Approved
0.6311	Remote Similarity	NPD6012	Approved
0.6311	Remote Similarity	NPD6014	Approved
0.631	Remote Similarity	NPD4190	Phase 3
0.631	Remote Similarity	NPD5275	Approved
0.6289	Remote Similarity	NPD7902	Approved
0.6289	Remote Similarity	NPD3495	Discontinued
0.6286	Remote Similarity	NPD6882	Approved
0.6286	Remote Similarity	NPD8297	Approved
0.6275	Remote Similarity	NPD5701	Approved
0.6275	Remote Similarity	NPD6412	Phase 2
0.625	Remote Similarity	NPD5169	Approved
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD4634	Approved
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD5249	Phase 3
0.625	Remote Similarity	NPD5135	Approved
0.625	Remote Similarity	NPD5247	Approved
0.625	Remote Similarity	NPD5251	Approved
0.625	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6939	Phase 2
0.622	Remote Similarity	NPD4789	Approved
0.622	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7115	Discovery
0.6203	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD7341	Phase 2
0.619	Remote Similarity	NPD5127	Approved
0.619	Remote Similarity	NPD5215	Approved
0.619	Remote Similarity	NPD5217	Approved
0.619	Remote Similarity	NPD5216	Approved
0.619	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1696	Phase 3
0.6145	Remote Similarity	NPD6081	Approved
0.6145	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7525	Registered
0.6125	Remote Similarity	NPD4224	Phase 2
0.6111	Remote Similarity	NPD6868	Approved
0.6098	Remote Similarity	NPD6923	Approved
0.6098	Remote Similarity	NPD6922	Approved
0.6092	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD4632	Approved
0.6064	Remote Similarity	NPD6051	Approved
0.6061	Remote Similarity	NPD7638	Approved
0.6042	Remote Similarity	NPD7631	Approved
0.6024	Remote Similarity	NPD7143	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