NPASS Compound

Structure

NPC476101 OpenBabel07101718322D 27 29 0 0 1 0 0 0 0 0999 V2000 -4.6888 -4.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2575 -2.3912 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 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7229 -3.9659 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 -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 -1.7321 -3.0000 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 0.8660 -0.5000 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 1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 3 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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 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 -0.8660 -1.5000 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 2.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 5 26 1 0 0 0 0 6 21 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 17 22 1 0 0 0 0 18 22 1 6 0 0 0 18 23 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 21 2 1 6 0 0 0 22 3 1 6 0 0 0 23 4 1 1 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.25
Volume:	405.31
LogP:	4.411
LogD:	3.642
LogS:	-5.186
# Rotatable Bonds:	6
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.396
Synthetic Accessibility Score:	4.581
Fsp3:	0.739
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.714
MDCK Permeability:	2.3196846086648293e-05
Pgp-inhibitor:	0.625
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.245
30% Bioavailability (F30%):	0.762

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.951
Plasma Protein Binding (PPB):	77.85869598388672%
Volume Distribution (VD):	0.86
Pgp-substrate:	17.177799224853516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.396
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.221
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.674

ADMET: Excretion

Clearance (CL):	6.101
Half-life (T1/2):	0.341

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.849
Skin Sensitization:	0.631
Carcinogencity:	0.501
Eye Corrosion:	0.828
Eye Irritation:	0.437
Respiratory Toxicity:	0.903

Download Data

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

Natural Product: NPC476101

Natural Product ID:	NPC476101
*Common Name:**	Methyl (1R,4Ar,7R,10As)-1,4A,7-Trimethyl-7-Vinyl-1,2,3,4,4A,6,7,8,8A,9,10,10A-Dodecahydrophenanthren-1-Yl Malonate
IUPAC Name:	3-O-[(1R,4aR,7R,10aS)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthren-1-yl] 1-O-methyl propanedioate
Synonyms:
Standard InCHIKey:	BYEMEEXQSBNVHR-MFKBGVJLSA-N
Standard InCHI:	InChI=1S/C23H34O4/c1-6-21(2)13-10-17-16(15-21)8-9-18-22(17,3)11-7-12-23(18,4)27-20(25)14-19(24)26-5/h6,10,16,18H,1,7-9,11-15H2,2-5H3/t16?,18-,21+,22-,23+/m0/s1
SMILES:	CC12CCCC(C1CCC3C2=CCC(C3)(C)C=C)(C)OC(=O)CC(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526303
PubChem CID:	44566218
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO33152	calceolaria pinifolia	Species	Calceolariaceae	Eukaryota	aerial part	46 km west of Puesto de Gendarmeria in the province of San Juan, Argentina (3021 S; 6940 W)	1997-Jan	PMID[12608857]

☑ 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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	128.0	ug.mL-1	PMID[550174]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[550174]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[550174]

☑ 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 NPC476101 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	203
0.1-0.2	1346
0.2-0.3	5478
0.3-0.4	16049
0.4-0.5	8228
0.5-0.6	6201
0.6-0.7	4479
0.7-0.8	702
0.8-0.85	7
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC474978
0.9487	High Similarity	NPC473592
0.9114	High Similarity	NPC474979
0.8395	Intermediate Similarity	NPC269791
0.8193	Intermediate Similarity	NPC286786
0.8118	Intermediate Similarity	NPC76333
0.8101	Intermediate Similarity	NPC166797
0.8095	Intermediate Similarity	NPC132386
0.8072	Intermediate Similarity	NPC142163
0.8072	Intermediate Similarity	NPC195334
0.8072	Intermediate Similarity	NPC290495
0.8049	Intermediate Similarity	NPC100906
0.8023	Intermediate Similarity	NPC73038
0.8	Intermediate Similarity	NPC474768
0.8	Intermediate Similarity	NPC23621
0.8	Intermediate Similarity	NPC78580
0.8	Intermediate Similarity	NPC184006
0.7931	Intermediate Similarity	NPC46912
0.7931	Intermediate Similarity	NPC162107
0.7927	Intermediate Similarity	NPC321514
0.7912	Intermediate Similarity	NPC195715
0.7912	Intermediate Similarity	NPC23241
0.7882	Intermediate Similarity	NPC52108
0.7882	Intermediate Similarity	NPC474789
0.7882	Intermediate Similarity	NPC476927
0.7857	Intermediate Similarity	NPC327002
0.7857	Intermediate Similarity	NPC476988
0.7857	Intermediate Similarity	NPC108476
0.7857	Intermediate Similarity	NPC474955
0.7831	Intermediate Similarity	NPC44083
0.7831	Intermediate Similarity	NPC28319
0.7831	Intermediate Similarity	NPC153987
0.7816	Intermediate Similarity	NPC329943
0.7816	Intermediate Similarity	NPC325594
0.7816	Intermediate Similarity	NPC474970
0.7816	Intermediate Similarity	NPC10005
0.7816	Intermediate Similarity	NPC262085
0.7816	Intermediate Similarity	NPC91525
0.7816	Intermediate Similarity	NPC286153
0.7816	Intermediate Similarity	NPC9892
0.7805	Intermediate Similarity	NPC472300
0.7802	Intermediate Similarity	NPC473431
0.7802	Intermediate Similarity	NPC473280
0.7802	Intermediate Similarity	NPC471078
0.7802	Intermediate Similarity	NPC473435
0.7791	Intermediate Similarity	NPC156981
0.7778	Intermediate Similarity	NPC282616
0.7778	Intermediate Similarity	NPC471588
0.7778	Intermediate Similarity	NPC288833
0.7778	Intermediate Similarity	NPC228784
0.7778	Intermediate Similarity	NPC6255
0.7778	Intermediate Similarity	NPC324341
0.7778	Intermediate Similarity	NPC155120
0.7778	Intermediate Similarity	NPC966
0.7765	Intermediate Similarity	NPC256112
0.7753	Intermediate Similarity	NPC474700
0.7753	Intermediate Similarity	NPC471342
0.7753	Intermediate Similarity	NPC469866
0.7753	Intermediate Similarity	NPC59682
0.7753	Intermediate Similarity	NPC475049
0.7753	Intermediate Similarity	NPC474570
0.7742	Intermediate Similarity	NPC26413
0.7738	Intermediate Similarity	NPC476265
0.7738	Intermediate Similarity	NPC267517
0.7738	Intermediate Similarity	NPC274522
0.7738	Intermediate Similarity	NPC104545
0.7738	Intermediate Similarity	NPC37038
0.7727	Intermediate Similarity	NPC171722
0.7727	Intermediate Similarity	NPC478104
0.7727	Intermediate Similarity	NPC30421
0.7727	Intermediate Similarity	NPC166857
0.7711	Intermediate Similarity	NPC4827
0.7701	Intermediate Similarity	NPC191965
0.7701	Intermediate Similarity	NPC474013
0.7701	Intermediate Similarity	NPC476602
0.7692	Intermediate Similarity	NPC86368
0.7683	Intermediate Similarity	NPC899
0.7674	Intermediate Similarity	NPC139206
0.7667	Intermediate Similarity	NPC471896
0.7667	Intermediate Similarity	NPC120840
0.7667	Intermediate Similarity	NPC86372
0.7667	Intermediate Similarity	NPC113989
0.7667	Intermediate Similarity	NPC474728
0.7667	Intermediate Similarity	NPC172361
0.766	Intermediate Similarity	NPC164349
0.7654	Intermediate Similarity	NPC71152
0.7647	Intermediate Similarity	NPC25554
0.7647	Intermediate Similarity	NPC170303
0.764	Intermediate Similarity	NPC224145
0.764	Intermediate Similarity	NPC474845
0.764	Intermediate Similarity	NPC93411
0.7634	Intermediate Similarity	NPC151725
0.7634	Intermediate Similarity	NPC106425
0.7634	Intermediate Similarity	NPC269492
0.7634	Intermediate Similarity	NPC132824
0.7634	Intermediate Similarity	NPC120708
0.7634	Intermediate Similarity	NPC98874
0.7634	Intermediate Similarity	NPC327788
0.7634	Intermediate Similarity	NPC122324
0.7619	Intermediate Similarity	NPC231431
0.7619	Intermediate Similarity	NPC327674
0.7614	Intermediate Similarity	NPC84121
0.7614	Intermediate Similarity	NPC264127
0.7614	Intermediate Similarity	NPC324063
0.7614	Intermediate Similarity	NPC137306
0.7609	Intermediate Similarity	NPC222047
0.7609	Intermediate Similarity	NPC148964
0.759	Intermediate Similarity	NPC132542
0.759	Intermediate Similarity	NPC283619
0.7586	Intermediate Similarity	NPC312660
0.7586	Intermediate Similarity	NPC306951
0.7586	Intermediate Similarity	NPC475193
0.7586	Intermediate Similarity	NPC120158
0.7582	Intermediate Similarity	NPC285184
0.7582	Intermediate Similarity	NPC177641
0.7582	Intermediate Similarity	NPC470590
0.7582	Intermediate Similarity	NPC60755
0.7582	Intermediate Similarity	NPC77099
0.7582	Intermediate Similarity	NPC476417
0.7579	Intermediate Similarity	NPC475202
0.7579	Intermediate Similarity	NPC473576
0.7579	Intermediate Similarity	NPC475385
0.7579	Intermediate Similarity	NPC475392
0.7579	Intermediate Similarity	NPC475156
0.7561	Intermediate Similarity	NPC192540
0.7561	Intermediate Similarity	NPC279666
0.7558	Intermediate Similarity	NPC15910
0.7558	Intermediate Similarity	NPC2524
0.7556	Intermediate Similarity	NPC293048
0.7556	Intermediate Similarity	NPC61543
0.7556	Intermediate Similarity	NPC59263
0.7556	Intermediate Similarity	NPC270768
0.7556	Intermediate Similarity	NPC234346
0.7556	Intermediate Similarity	NPC177141
0.7556	Intermediate Similarity	NPC16265
0.7556	Intermediate Similarity	NPC475921
0.7556	Intermediate Similarity	NPC225585
0.7556	Intermediate Similarity	NPC130520
0.7556	Intermediate Similarity	NPC121798
0.7556	Intermediate Similarity	NPC263393
0.7556	Intermediate Similarity	NPC30522
0.7556	Intermediate Similarity	NPC127689
0.7556	Intermediate Similarity	NPC474704
0.7553	Intermediate Similarity	NPC473456
0.7553	Intermediate Similarity	NPC89225
0.7529	Intermediate Similarity	NPC469802
0.7529	Intermediate Similarity	NPC233332
0.7529	Intermediate Similarity	NPC477057
0.7528	Intermediate Similarity	NPC158141
0.7528	Intermediate Similarity	NPC125925
0.7528	Intermediate Similarity	NPC96496
0.7528	Intermediate Similarity	NPC173089
0.7527	Intermediate Similarity	NPC148523
0.7527	Intermediate Similarity	NPC476519
0.75	Intermediate Similarity	NPC260385
0.75	Intermediate Similarity	NPC2709
0.75	Intermediate Similarity	NPC93744
0.75	Intermediate Similarity	NPC79117
0.75	Intermediate Similarity	NPC476888
0.75	Intermediate Similarity	NPC110094
0.75	Intermediate Similarity	NPC38232
0.75	Intermediate Similarity	NPC470223
0.75	Intermediate Similarity	NPC280654
0.75	Intermediate Similarity	NPC298554
0.75	Intermediate Similarity	NPC179028
0.75	Intermediate Similarity	NPC164424
0.75	Intermediate Similarity	NPC118490
0.7474	Intermediate Similarity	NPC174663
0.7473	Intermediate Similarity	NPC130278
0.7473	Intermediate Similarity	NPC470589
0.7473	Intermediate Similarity	NPC126369
0.7473	Intermediate Similarity	NPC148414
0.7473	Intermediate Similarity	NPC8062
0.7473	Intermediate Similarity	NPC474842
0.7473	Intermediate Similarity	NPC76286
0.7473	Intermediate Similarity	NPC328141
0.7473	Intermediate Similarity	NPC175628
0.7473	Intermediate Similarity	NPC475965
0.7473	Intermediate Similarity	NPC111110
0.7473	Intermediate Similarity	NPC111585
0.7471	Intermediate Similarity	NPC476100
0.7471	Intermediate Similarity	NPC200752
0.7471	Intermediate Similarity	NPC477373
0.747	Intermediate Similarity	NPC69143
0.7447	Intermediate Similarity	NPC167193
0.7447	Intermediate Similarity	NPC201657
0.7447	Intermediate Similarity	NPC327179
0.7447	Intermediate Similarity	NPC472806
0.7447	Intermediate Similarity	NPC471153
0.7444	Intermediate Similarity	NPC472220
0.7444	Intermediate Similarity	NPC80335
0.7444	Intermediate Similarity	NPC246708
0.7444	Intermediate Similarity	NPC1753
0.7444	Intermediate Similarity	NPC40552
0.7444	Intermediate Similarity	NPC473879
0.7444	Intermediate Similarity	NPC182797
0.7444	Intermediate Similarity	NPC477128
0.7444	Intermediate Similarity	NPC97884
0.7444	Intermediate Similarity	NPC52169
0.7444	Intermediate Similarity	NPC474511

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 NPC476101 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1535
0.2-0.3	4211
0.3-0.4	2252
0.4-0.5	568
0.5-0.6	207
0.6-0.7	168
0.7-0.8	22
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
0.7727	Intermediate Similarity	NPD3573	Approved
0.7527	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5737	Approved
0.7444	Intermediate Similarity	NPD6672	Approved
0.7419	Intermediate Similarity	NPD7748	Approved
0.7419	Intermediate Similarity	NPD7900	Approved
0.7419	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7334	Approved
0.7416	Intermediate Similarity	NPD6098	Approved
0.7416	Intermediate Similarity	NPD7146	Approved
0.7416	Intermediate Similarity	NPD6409	Approved
0.7416	Intermediate Similarity	NPD6684	Approved
0.7416	Intermediate Similarity	NPD7521	Approved
0.7416	Intermediate Similarity	NPD5330	Approved
0.7391	Intermediate Similarity	NPD6411	Approved
0.7363	Intermediate Similarity	NPD6080	Approved
0.7363	Intermediate Similarity	NPD6904	Approved
0.7363	Intermediate Similarity	NPD6673	Approved
0.7363	Intermediate Similarity	NPD6051	Approved
0.7253	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6903	Approved
0.7209	Intermediate Similarity	NPD7645	Phase 2
0.7204	Intermediate Similarity	NPD7515	Phase 2
0.7188	Intermediate Similarity	NPD6083	Phase 2
0.7188	Intermediate Similarity	NPD7902	Approved
0.7188	Intermediate Similarity	NPD6084	Phase 2
0.7174	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6101	Approved
0.7128	Intermediate Similarity	NPD6399	Phase 3
0.7065	Intermediate Similarity	NPD5208	Approved
0.7059	Intermediate Similarity	NPD6881	Approved
0.7059	Intermediate Similarity	NPD6899	Approved
0.7053	Intermediate Similarity	NPD6001	Approved
0.7033	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5739	Approved
0.703	Intermediate Similarity	NPD6402	Approved
0.703	Intermediate Similarity	NPD6675	Approved
0.703	Intermediate Similarity	NPD7128	Approved
0.7021	Intermediate Similarity	NPD6050	Approved
0.7021	Intermediate Similarity	NPD5693	Phase 1
0.7021	Intermediate Similarity	NPD5694	Approved
0.6979	Remote Similarity	NPD5695	Phase 3
0.6966	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5697	Approved
0.6939	Remote Similarity	NPD5696	Approved
0.6939	Remote Similarity	NPD4225	Approved
0.6939	Remote Similarity	NPD7638	Approved
0.6932	Remote Similarity	NPD7525	Registered
0.6923	Remote Similarity	NPD7102	Approved
0.6923	Remote Similarity	NPD6883	Approved
0.6923	Remote Similarity	NPD7290	Approved
0.6915	Remote Similarity	NPD5692	Phase 3
0.6915	Remote Similarity	NPD5207	Approved
0.6893	Remote Similarity	NPD7320	Approved
0.6869	Remote Similarity	NPD7639	Approved
0.6869	Remote Similarity	NPD7640	Approved
0.6857	Remote Similarity	NPD6650	Approved
0.6857	Remote Similarity	NPD6617	Approved
0.6857	Remote Similarity	NPD6649	Approved
0.6857	Remote Similarity	NPD6869	Approved
0.6857	Remote Similarity	NPD6847	Approved
0.6857	Remote Similarity	NPD8130	Phase 1
0.6852	Remote Similarity	NPD7115	Discovery
0.6842	Remote Similarity	NPD7637	Suspended
0.6827	Remote Similarity	NPD6012	Approved
0.6827	Remote Similarity	NPD6373	Approved
0.6827	Remote Similarity	NPD6013	Approved
0.6827	Remote Similarity	NPD6014	Approved
0.6827	Remote Similarity	NPD6372	Approved
0.6824	Remote Similarity	NPD4784	Approved
0.6824	Remote Similarity	NPD4785	Approved
0.6818	Remote Similarity	NPD4195	Approved
0.6796	Remote Similarity	NPD5701	Approved
0.6792	Remote Similarity	NPD6882	Approved
0.6792	Remote Similarity	NPD8297	Approved
0.6786	Remote Similarity	NPD4243	Approved
0.6771	Remote Similarity	NPD5779	Approved
0.6771	Remote Similarity	NPD5778	Approved
0.6739	Remote Similarity	NPD1694	Approved
0.6731	Remote Similarity	NPD6011	Approved
0.6699	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6079	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6632	Remote Similarity	NPD4753	Phase 2
0.6632	Remote Similarity	NPD5328	Approved
0.6632	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4786	Approved
0.663	Remote Similarity	NPD3668	Phase 3
0.6593	Remote Similarity	NPD4221	Approved
0.6593	Remote Similarity	NPD4223	Phase 3
0.6593	Remote Similarity	NPD3667	Approved
0.6566	Remote Similarity	NPD7732	Phase 3
0.6559	Remote Similarity	NPD5329	Approved
0.6559	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4695	Discontinued
0.6552	Remote Similarity	NPD8039	Approved
0.6552	Remote Similarity	NPD7339	Approved
0.6552	Remote Similarity	NPD6942	Approved
0.6542	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4696	Approved
0.6535	Remote Similarity	NPD5286	Approved
0.6535	Remote Similarity	NPD5285	Approved
0.6531	Remote Similarity	NPD5707	Approved
0.6518	Remote Similarity	NPD6319	Approved
0.6505	Remote Similarity	NPD6052	Approved
0.65	Remote Similarity	NPD4755	Approved
0.6489	Remote Similarity	NPD4519	Discontinued
0.6489	Remote Similarity	NPD4623	Approved
0.6477	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6614	Approved
0.6465	Remote Similarity	NPD5654	Approved
0.6465	Remote Similarity	NPD4629	Approved
0.6465	Remote Similarity	NPD5210	Approved
0.6452	Remote Similarity	NPD3665	Phase 1
0.6452	Remote Similarity	NPD3666	Approved
0.6452	Remote Similarity	NPD3133	Approved
0.6452	Remote Similarity	NPD4197	Approved
0.6435	Remote Similarity	NPD7492	Approved
0.6429	Remote Similarity	NPD4202	Approved
0.6429	Remote Similarity	NPD7101	Approved
0.6429	Remote Similarity	NPD7100	Approved
0.6415	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5211	Phase 2
0.6408	Remote Similarity	NPD5224	Approved
0.6408	Remote Similarity	NPD4633	Approved
0.6408	Remote Similarity	NPD5225	Approved
0.6408	Remote Similarity	NPD5226	Approved
0.64	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5222	Approved
0.64	Remote Similarity	NPD5221	Approved
0.6379	Remote Similarity	NPD6616	Approved
0.6373	Remote Similarity	NPD4700	Approved
0.6372	Remote Similarity	NPD6054	Approved
0.6364	Remote Similarity	NPD5275	Approved
0.6364	Remote Similarity	NPD4190	Phase 3
0.6353	Remote Similarity	NPD4137	Phase 3
0.6346	Remote Similarity	NPD5175	Approved
0.6346	Remote Similarity	NPD5174	Approved
0.6344	Remote Similarity	NPD6695	Phase 3
0.6341	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6335	Approved
0.6337	Remote Similarity	NPD5173	Approved
0.6337	Remote Similarity	NPD5959	Approved
0.6325	Remote Similarity	NPD7078	Approved
0.6321	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4689	Approved
0.6316	Remote Similarity	NPD4693	Phase 3
0.6316	Remote Similarity	NPD4690	Approved
0.6316	Remote Similarity	NPD5690	Phase 2
0.6316	Remote Similarity	NPD4688	Approved
0.6316	Remote Similarity	NPD5205	Approved
0.6316	Remote Similarity	NPD4138	Approved
0.6311	Remote Similarity	NPD5223	Approved
0.6306	Remote Similarity	NPD6868	Approved
0.6306	Remote Similarity	NPD6274	Approved
0.6296	Remote Similarity	NPD4634	Approved
0.6286	Remote Similarity	NPD5141	Approved
0.6279	Remote Similarity	NPD4691	Approved
0.6279	Remote Similarity	NPD4747	Approved
0.6277	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4632	Approved
0.6271	Remote Similarity	NPD7736	Approved
0.6261	Remote Similarity	NPD6370	Approved
0.625	Remote Similarity	NPD6317	Approved
0.625	Remote Similarity	NPD6926	Approved
0.625	Remote Similarity	NPD4058	Approved
0.625	Remote Similarity	NPD7632	Discontinued
0.625	Remote Similarity	NPD6924	Approved
0.6238	Remote Similarity	NPD7614	Phase 1
0.6238	Remote Similarity	NPD4697	Phase 3
0.6238	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6059	Approved
0.6207	Remote Similarity	NPD8328	Phase 3
0.6204	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6313	Approved
0.6195	Remote Similarity	NPD6314	Approved
0.6186	Remote Similarity	NPD8293	Discontinued
0.6174	Remote Similarity	NPD6908	Approved
0.6174	Remote Similarity	NPD6015	Approved
0.6174	Remote Similarity	NPD7503	Approved
0.6174	Remote Similarity	NPD6016	Approved
0.6174	Remote Similarity	NPD6909	Approved
0.6168	Remote Similarity	NPD6412	Phase 2
0.6154	Remote Similarity	NPD3617	Approved
0.6147	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4694	Approved
0.6146	Remote Similarity	NPD5280	Approved
0.6129	Remote Similarity	NPD5369	Approved
0.6121	Remote Similarity	NPD5988	Approved
0.6111	Remote Similarity	NPD6933	Approved
0.6111	Remote Similarity	NPD4729	Approved
0.6111	Remote Similarity	NPD6686	Approved
0.6111	Remote Similarity	NPD4730	Approved
0.6106	Remote Similarity	NPD8295	Clinical (unspecified phase)

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