NPASS Compound

Structure

NPC76312 OpenBabel07101718182D 29 33 0 0 1 0 0 0 0 0999 V2000 -5.0372 -4.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4062 -3.8827 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 -1.7321 0.0000 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 -0.0000 -2.0000 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 0.8660 -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 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 -3.4641 -3.0000 0.0000 C 0 0 1 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 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 23 1 0 0 0 0 2 23 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 6 18 2 0 0 0 0 7 19 2 0 0 0 0 8 12 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 21 1 0 0 0 0 10 23 1 0 0 0 0 11 26 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 27 2 0 0 0 0 17 19 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 23 1 0 0 0 0 20 26 1 1 0 0 0 21 24 1 1 0 0 0 21 26 1 0 0 0 0 22 24 1 1 0 0 0 22 25 1 0 0 0 0 24 3 1 1 0 0 0 25 4 1 1 0 0 0 25 29 1 0 0 0 0 26 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.27
Volume:	431.295
LogP:	5.579
LogD:	4.714
LogS:	-4.1
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.599
Synthetic Accessibility Score:	4.509
Fsp3:	0.731
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.873
MDCK Permeability:	1.2002423318335786e-05
Pgp-inhibitor:	0.452
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.943
Plasma Protein Binding (PPB):	79.3175277709961%
Volume Distribution (VD):	2.612
Pgp-substrate:	10.050415992736816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.153
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.697
CYP2C9-inhibitor:	0.245
CYP2C9-substrate:	0.423
CYP2D6-inhibitor:	0.931
CYP2D6-substrate:	0.754
CYP3A4-inhibitor:	0.927
CYP3A4-substrate:	0.401

ADMET: Excretion

Clearance (CL):	10.78
Half-life (T1/2):	0.144

ADMET: Toxicity

hERG Blockers:	0.431
Human Hepatotoxicity (H-HT):	0.267
Drug-inuced Liver Injury (DILI):	0.063
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.123
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.962
Carcinogencity:	0.288
Eye Corrosion:	0.63
Eye Irritation:	0.896
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC76312

Natural Product ID:	NPC76312
*Common Name:**	Strongylophorine-24
IUPAC Name:	n.a.
Synonyms:	Strongylophorine-24
Standard InCHIKey:	RYXAKJYTPYDEOI-SQRMQMBQSA-N
Standard InCHI:	InChI=1S/C26H36O3/c1-23(2)10-5-11-26(16-27)20(23)8-12-24(3)21(26)9-13-25(4)22(24)15-17-14-18(28)6-7-19(17)29-25/h6-7,14,16,20-22,28H,5,8-13,15H2,1-4H3/t20-,21-,22-,24+,25-,26+/m0/s1
SMILES:	CC1(C)CCC[C@@]2(C=O)[C@H]1CC[C@]1(C)[C@@H]2CC[C@@]2(C)[C@H]1Cc1cc(ccc1O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469078
PubChem CID:	11463618
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003557] 19-oxosteroids

*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
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350165]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	Okinawan, Japan	n.a.	PMID[14695804]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332859]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17407351]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[25987373]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7807132]
NPO24364	Petrosia corticata	Species	Petrosiidae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[520472]

☑ 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 NPC76312 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	353
0.1-0.2	1508
0.2-0.3	2782
0.3-0.4	7247
0.4-0.5	10909
0.5-0.6	6376
0.6-0.7	11761
0.7-0.8	1715
0.8-0.85	25
0.85-0.9	11
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9624	High Similarity	NPC474610
0.942	High Similarity	NPC474599
0.9412	High Similarity	NPC79372
0.9338	High Similarity	NPC265335
0.9248	High Similarity	NPC153019
0.9167	High Similarity	NPC47288
0.9111	High Similarity	NPC211352
0.9037	High Similarity	NPC289624
0.9037	High Similarity	NPC27578
0.8864	High Similarity	NPC248557
0.8723	High Similarity	NPC473049
0.8723	High Similarity	NPC472794
0.8705	High Similarity	NPC279463
0.8686	High Similarity	NPC258073
0.8676	High Similarity	NPC206028
0.8662	High Similarity	NPC472791
0.8662	High Similarity	NPC472792
0.8636	High Similarity	NPC475839
0.8603	High Similarity	NPC176590
0.8456	Intermediate Similarity	NPC128321
0.8444	Intermediate Similarity	NPC190086
0.8444	Intermediate Similarity	NPC276962
0.8421	Intermediate Similarity	NPC469507
0.8417	Intermediate Similarity	NPC474143
0.8417	Intermediate Similarity	NPC474246
0.8345	Intermediate Similarity	NPC475880
0.8322	Intermediate Similarity	NPC98804
0.8309	Intermediate Similarity	NPC147896
0.8278	Intermediate Similarity	NPC48671
0.8271	Intermediate Similarity	NPC51341
0.8252	Intermediate Similarity	NPC194847
0.8252	Intermediate Similarity	NPC21797
0.8239	Intermediate Similarity	NPC27394
0.8231	Intermediate Similarity	NPC316691
0.8227	Intermediate Similarity	NPC85595
0.8222	Intermediate Similarity	NPC253627
0.8222	Intermediate Similarity	NPC168707
0.8222	Intermediate Similarity	NPC48623
0.8214	Intermediate Similarity	NPC475102
0.8214	Intermediate Similarity	NPC196621
0.8209	Intermediate Similarity	NPC474131
0.8176	Intermediate Similarity	NPC471600
0.8175	Intermediate Similarity	NPC61685
0.8175	Intermediate Similarity	NPC474237
0.8163	Intermediate Similarity	NPC329493
0.8162	Intermediate Similarity	NPC11250
0.8153	Intermediate Similarity	NPC140346
0.8148	Intermediate Similarity	NPC45663
0.8134	Intermediate Similarity	NPC471449
0.8134	Intermediate Similarity	NPC32152
0.812	Intermediate Similarity	NPC238176
0.812	Intermediate Similarity	NPC187993
0.8099	Intermediate Similarity	NPC251549
0.8095	Intermediate Similarity	NPC186033
0.8088	Intermediate Similarity	NPC476165
0.8085	Intermediate Similarity	NPC249425
0.8085	Intermediate Similarity	NPC473048
0.8085	Intermediate Similarity	NPC472793
0.8082	Intermediate Similarity	NPC476191
0.8074	Intermediate Similarity	NPC232295
0.8056	Intermediate Similarity	NPC477874
0.8056	Intermediate Similarity	NPC173569
0.8054	Intermediate Similarity	NPC169942
0.8054	Intermediate Similarity	NPC90645
0.8045	Intermediate Similarity	NPC69539
0.8043	Intermediate Similarity	NPC75432
0.8028	Intermediate Similarity	NPC473047
0.8014	Intermediate Similarity	NPC202260
0.8014	Intermediate Similarity	NPC59654
0.8013	Intermediate Similarity	NPC272196
0.8	Intermediate Similarity	NPC471608
0.8	Intermediate Similarity	NPC249817
0.7986	Intermediate Similarity	NPC133407
0.7986	Intermediate Similarity	NPC477210
0.7986	Intermediate Similarity	NPC137750
0.7986	Intermediate Similarity	NPC28476
0.7986	Intermediate Similarity	NPC477213
0.7974	Intermediate Similarity	NPC118033
0.7973	Intermediate Similarity	NPC263337
0.7973	Intermediate Similarity	NPC323126
0.7971	Intermediate Similarity	NPC261992
0.7971	Intermediate Similarity	NPC471187
0.7962	Intermediate Similarity	NPC472617
0.7958	Intermediate Similarity	NPC196193
0.7958	Intermediate Similarity	NPC470725
0.7945	Intermediate Similarity	NPC130976
0.7945	Intermediate Similarity	NPC475482
0.7945	Intermediate Similarity	NPC22676
0.7945	Intermediate Similarity	NPC216940
0.7945	Intermediate Similarity	NPC198621
0.7941	Intermediate Similarity	NPC135467
0.7941	Intermediate Similarity	NPC260832
0.7933	Intermediate Similarity	NPC472457
0.7931	Intermediate Similarity	NPC475011
0.7926	Intermediate Similarity	NPC139047
0.7922	Intermediate Similarity	NPC475579
0.7922	Intermediate Similarity	NPC473773
0.7919	Intermediate Similarity	NPC474154
0.791	Intermediate Similarity	NPC141001
0.7905	Intermediate Similarity	NPC172311
0.7902	Intermediate Similarity	NPC474200
0.7899	Intermediate Similarity	NPC46586
0.7899	Intermediate Similarity	NPC476332
0.7899	Intermediate Similarity	NPC188997
0.7899	Intermediate Similarity	NPC473464
0.7899	Intermediate Similarity	NPC204535
0.7899	Intermediate Similarity	NPC478058
0.7895	Intermediate Similarity	NPC212142
0.7891	Intermediate Similarity	NPC234548
0.7891	Intermediate Similarity	NPC248287
0.7887	Intermediate Similarity	NPC271832
0.7887	Intermediate Similarity	NPC96719
0.7887	Intermediate Similarity	NPC222108
0.7883	Intermediate Similarity	NPC129176
0.7877	Intermediate Similarity	NPC278832
0.7877	Intermediate Similarity	NPC307401
0.7877	Intermediate Similarity	NPC64157
0.7872	Intermediate Similarity	NPC319422
0.7872	Intermediate Similarity	NPC477212
0.7872	Intermediate Similarity	NPC477214
0.7872	Intermediate Similarity	NPC95034
0.7872	Intermediate Similarity	NPC142087
0.7872	Intermediate Similarity	NPC186889
0.7872	Intermediate Similarity	NPC477211
0.7871	Intermediate Similarity	NPC105942
0.7871	Intermediate Similarity	NPC205392
0.7867	Intermediate Similarity	NPC25491
0.7862	Intermediate Similarity	NPC265793
0.7862	Intermediate Similarity	NPC71372
0.7862	Intermediate Similarity	NPC213122
0.7857	Intermediate Similarity	NPC475890
0.7857	Intermediate Similarity	NPC475454
0.7857	Intermediate Similarity	NPC473579
0.7857	Intermediate Similarity	NPC320847
0.7857	Intermediate Similarity	NPC473680
0.7857	Intermediate Similarity	NPC475311
0.7857	Intermediate Similarity	NPC137416
0.7848	Intermediate Similarity	NPC239118
0.7847	Intermediate Similarity	NPC329427
0.7847	Intermediate Similarity	NPC118253
0.7847	Intermediate Similarity	NPC472798
0.7847	Intermediate Similarity	NPC317601
0.7847	Intermediate Similarity	NPC165612
0.7842	Intermediate Similarity	NPC474130
0.7842	Intermediate Similarity	NPC198014
0.7838	Intermediate Similarity	NPC252901
0.7838	Intermediate Similarity	NPC221134
0.7836	Intermediate Similarity	NPC473718
0.7829	Intermediate Similarity	NPC211565
0.7829	Intermediate Similarity	NPC477208
0.7817	Intermediate Similarity	NPC201419
0.7808	Intermediate Similarity	NPC252343
0.7808	Intermediate Similarity	NPC472804
0.7806	Intermediate Similarity	NPC325860
0.7803	Intermediate Similarity	NPC275627
0.7803	Intermediate Similarity	NPC77772
0.78	Intermediate Similarity	NPC477873
0.78	Intermediate Similarity	NPC197461
0.78	Intermediate Similarity	NPC469447
0.7799	Intermediate Similarity	NPC472618
0.7794	Intermediate Similarity	NPC283616
0.7793	Intermediate Similarity	NPC49742
0.7792	Intermediate Similarity	NPC158784
0.7792	Intermediate Similarity	NPC195561
0.7786	Intermediate Similarity	NPC265413
0.7786	Intermediate Similarity	NPC181334
0.7786	Intermediate Similarity	NPC10154
0.7785	Intermediate Similarity	NPC472801
0.7785	Intermediate Similarity	NPC44199
0.7785	Intermediate Similarity	NPC158542
0.7785	Intermediate Similarity	NPC304110
0.7785	Intermediate Similarity	NPC27518
0.7778	Intermediate Similarity	NPC236070
0.7778	Intermediate Similarity	NPC125465
0.7778	Intermediate Similarity	NPC242580
0.7778	Intermediate Similarity	NPC251336
0.7778	Intermediate Similarity	NPC472590
0.7778	Intermediate Similarity	NPC126759
0.7771	Intermediate Similarity	NPC478050
0.777	Intermediate Similarity	NPC121168
0.777	Intermediate Similarity	NPC152946
0.777	Intermediate Similarity	NPC475028
0.777	Intermediate Similarity	NPC476025
0.777	Intermediate Similarity	NPC76032
0.777	Intermediate Similarity	NPC132723
0.777	Intermediate Similarity	NPC49441
0.7762	Intermediate Similarity	NPC86257
0.7762	Intermediate Similarity	NPC472797
0.7762	Intermediate Similarity	NPC131684
0.7756	Intermediate Similarity	NPC44606
0.7755	Intermediate Similarity	NPC472800
0.7754	Intermediate Similarity	NPC212559
0.7754	Intermediate Similarity	NPC32322
0.7754	Intermediate Similarity	NPC259703
0.775	Intermediate Similarity	NPC18380
0.775	Intermediate Similarity	NPC137232
0.7748	Intermediate Similarity	NPC209085
0.7748	Intermediate Similarity	NPC224884
0.7748	Intermediate Similarity	NPC158871
0.7744	Intermediate Similarity	NPC62867

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 NPC76312 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	917
0.2-0.3	1404
0.3-0.4	2523
0.4-0.5	2168
0.5-0.6	1180
0.6-0.7	578
0.7-0.8	59
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8194	Intermediate Similarity	NPD6099	Approved
0.8194	Intermediate Similarity	NPD6100	Approved
0.8106	Intermediate Similarity	NPD6671	Approved
0.7902	Intermediate Similarity	NPD8032	Phase 2
0.7872	Intermediate Similarity	NPD2861	Phase 2
0.7852	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD7003	Approved
0.7832	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6273	Approved
0.7808	Intermediate Similarity	NPD7097	Phase 1
0.7786	Intermediate Similarity	NPD6696	Suspended
0.7778	Intermediate Similarity	NPD7340	Approved
0.7763	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD8166	Discontinued
0.7724	Intermediate Similarity	NPD4140	Approved
0.7714	Intermediate Similarity	NPD5327	Phase 3
0.7681	Intermediate Similarity	NPD3019	Approved
0.7655	Intermediate Similarity	NPD6663	Approved
0.7639	Intermediate Similarity	NPD7095	Approved
0.7622	Intermediate Similarity	NPD5736	Approved
0.7619	Intermediate Similarity	NPD6353	Approved
0.7609	Intermediate Similarity	NPD5585	Approved
0.7606	Intermediate Similarity	NPD2797	Approved
0.7603	Intermediate Similarity	NPD4060	Phase 1
0.7586	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4908	Phase 1
0.7564	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7458	Discontinued
0.7556	Intermediate Similarity	NPD1398	Phase 1
0.7554	Intermediate Similarity	NPD2932	Approved
0.7554	Intermediate Similarity	NPD1778	Approved
0.7551	Intermediate Similarity	NPD6355	Discontinued
0.7551	Intermediate Similarity	NPD5735	Approved
0.7535	Intermediate Similarity	NPD1283	Approved
0.7531	Intermediate Similarity	NPD8127	Discontinued
0.7517	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD3496	Discontinued
0.7482	Intermediate Similarity	NPD1651	Approved
0.7467	Intermediate Similarity	NPD2935	Discontinued
0.7466	Intermediate Similarity	NPD6798	Discontinued
0.7465	Intermediate Similarity	NPD4749	Approved
0.7431	Intermediate Similarity	NPD4624	Approved
0.7423	Intermediate Similarity	NPD6959	Discontinued
0.7417	Intermediate Similarity	NPD2346	Discontinued
0.7415	Intermediate Similarity	NPD6233	Phase 2
0.7394	Intermediate Similarity	NPD1608	Approved
0.7386	Intermediate Similarity	NPD4110	Phase 3
0.7386	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2979	Phase 3
0.7351	Intermediate Similarity	NPD4476	Approved
0.7351	Intermediate Similarity	NPD4477	Approved
0.7347	Intermediate Similarity	NPD3268	Approved
0.7347	Intermediate Similarity	NPD7985	Registered
0.7343	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4359	Approved
0.7338	Intermediate Similarity	NPD7644	Approved
0.7329	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7427	Discontinued
0.7324	Intermediate Similarity	NPD1610	Phase 2
0.7324	Intermediate Similarity	NPD1281	Approved
0.7324	Intermediate Similarity	NPD1611	Approved
0.7324	Intermediate Similarity	NPD1535	Discovery
0.731	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4626	Approved
0.7303	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD968	Approved
0.7278	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1481	Phase 2
0.7267	Intermediate Similarity	NPD4097	Suspended
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7262	Intermediate Similarity	NPD5844	Phase 1
0.7255	Intermediate Similarity	NPD7037	Approved
0.7248	Intermediate Similarity	NPD3620	Phase 2
0.7248	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5691	Approved
0.723	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7635	Approved
0.7208	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4622	Approved
0.72	Intermediate Similarity	NPD4618	Approved
0.7197	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7157	Approved
0.7192	Intermediate Similarity	NPD6584	Phase 3
0.719	Intermediate Similarity	NPD5762	Approved
0.719	Intermediate Similarity	NPD5763	Approved
0.719	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD17	Approved
0.7178	Intermediate Similarity	NPD7768	Phase 2
0.7171	Intermediate Similarity	NPD2799	Discontinued
0.7169	Intermediate Similarity	NPD3787	Discontinued
0.7163	Intermediate Similarity	NPD1894	Discontinued
0.7163	Intermediate Similarity	NPD3091	Approved
0.7161	Intermediate Similarity	NPD4628	Phase 3
0.716	Intermediate Similarity	NPD5929	Approved
0.716	Intermediate Similarity	NPD7819	Suspended
0.716	Intermediate Similarity	NPD5760	Phase 2
0.716	Intermediate Similarity	NPD5761	Phase 2
0.716	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2232	Approved
0.7153	Intermediate Similarity	NPD2233	Approved
0.7153	Intermediate Similarity	NPD2230	Approved
0.7151	Intermediate Similarity	NPD8313	Approved
0.7151	Intermediate Similarity	NPD8312	Approved
0.7133	Intermediate Similarity	NPD3026	Approved
0.7133	Intermediate Similarity	NPD3023	Approved
0.7125	Intermediate Similarity	NPD3226	Approved
0.7114	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3024	Approved
0.7113	Intermediate Similarity	NPD3025	Approved
0.7105	Intermediate Similarity	NPD5689	Approved
0.7105	Intermediate Similarity	NPD5688	Approved
0.7101	Intermediate Similarity	NPD7228	Approved
0.7099	Intermediate Similarity	NPD6844	Discontinued
0.7097	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6674	Discontinued
0.7089	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7028	Phase 2
0.7078	Intermediate Similarity	NPD6002	Phase 3
0.7078	Intermediate Similarity	NPD6005	Phase 3
0.7078	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6004	Phase 3
0.7075	Intermediate Similarity	NPD2798	Approved
0.7067	Intermediate Similarity	NPD4870	Approved
0.7066	Intermediate Similarity	NPD7229	Phase 3
0.7062	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7033	Discontinued
0.7059	Intermediate Similarity	NPD4308	Phase 3
0.7055	Intermediate Similarity	NPD8651	Approved
0.7051	Intermediate Similarity	NPD3750	Approved
0.705	Intermediate Similarity	NPD1241	Discontinued
0.7045	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6090	Discontinued
0.7039	Intermediate Similarity	NPD6653	Approved
0.7037	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6677	Suspended
0.7034	Intermediate Similarity	NPD3972	Approved
0.7032	Intermediate Similarity	NPD4534	Discontinued
0.7027	Intermediate Similarity	NPD2237	Approved
0.7025	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7041	Phase 2
0.7013	Intermediate Similarity	NPD2438	Suspended
0.7013	Intermediate Similarity	NPD2531	Phase 2
0.7012	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3267	Approved
0.7007	Intermediate Similarity	NPD3266	Approved
0.7	Intermediate Similarity	NPD2313	Discontinued
0.7	Intermediate Similarity	NPD7294	Phase 1
0.6994	Remote Similarity	NPD37	Approved
0.6994	Remote Similarity	NPD7577	Discontinued
0.6994	Remote Similarity	NPD1934	Approved
0.6988	Remote Similarity	NPD6234	Discontinued
0.6986	Remote Similarity	NPD6583	Phase 3
0.6986	Remote Similarity	NPD6582	Phase 2
0.6982	Remote Similarity	NPD6166	Phase 2
0.6982	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2614	Approved
0.6978	Remote Similarity	NPD5535	Approved
0.6971	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4967	Phase 2
0.697	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4965	Approved
0.697	Remote Similarity	NPD4966	Approved
0.6968	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2344	Approved
0.6968	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3092	Approved
0.6966	Remote Similarity	NPD1201	Approved
0.6951	Remote Similarity	NPD2801	Approved
0.6949	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5494	Approved
0.6944	Remote Similarity	NPD4059	Approved
0.6943	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2684	Approved
0.6933	Remote Similarity	NPD7411	Suspended
0.6932	Remote Similarity	NPD8434	Phase 2
0.6928	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7833	Phase 2
0.6928	Remote Similarity	NPD7831	Phase 2
0.6923	Remote Similarity	NPD2897	Discontinued
0.6923	Remote Similarity	NPD2424	Discontinued
0.6923	Remote Similarity	NPD1549	Phase 2
0.6923	Remote Similarity	NPD1548	Phase 1
0.6918	Remote Similarity	NPD2235	Phase 2
0.6918	Remote Similarity	NPD2231	Phase 2
0.691	Remote Similarity	NPD2490	Approved
0.691	Remote Similarity	NPD2488	Approved
0.6908	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1613	Approved
0.6908	Remote Similarity	NPD2238	Phase 2
0.6903	Remote Similarity	NPD6032	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