NPASS Compound

Structure

NPC473592 OpenBabel07101718192D 26 28 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 -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 1.0000 3.4641 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 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 5 20 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 16 2 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 17 21 1 6 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 25 2 0 0 0 0 19 26 1 0 0 0 0 20 2 1 6 0 0 0 21 3 1 6 0 0 0 22 4 1 1 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	388.014
LogP:	4.096
LogD:	2.632
LogS:	-4.643
# Rotatable Bonds:	5
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	4.603
Fsp3:	0.727
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:	-5.208
MDCK Permeability:	2.1558125808951445e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.839
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.854
Plasma Protein Binding (PPB):	90.99250793457031%
Volume Distribution (VD):	0.261
Pgp-substrate:	9.523262023925781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.268
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.756
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.447
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.753
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	2.262
Half-life (T1/2):	0.621

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.64
Skin Sensitization:	0.393
Carcinogencity:	0.496
Eye Corrosion:	0.904
Eye Irritation:	0.479
Respiratory Toxicity:	0.843

Download Data

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

Natural Product: NPC473592

Natural Product ID:	NPC473592
*Common Name:**	3-[[(1R,4Ar,7R,10As)-7-Ethenyl-1,4A,7-Trimethyl-3,4,6,8,8A,9,10,10A-Octahydro-2H-Phenanthren-1-Yl]Oxy]-3-Oxopropanoic Acid
IUPAC Name:	3-[[(1R,4aR,7R,10aS)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthren-1-yl]oxy]-3-oxopropanoic acid
Synonyms:
Standard InCHIKey:	BTAAEEJRNAVSQS-XJCCISBASA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-5-20(2)12-9-16-15(14-20)7-8-17-21(16,3)10-6-11-22(17,4)26-19(25)13-18(23)24/h5,9,15,17H,1,6-8,10-14H2,2-4H3,(H,23,24)/t15?,17-,20+,21-,22+/m0/s1
SMILES:	C=C[C@]1(C)CC=C2C(C1)CC[C@H]1[C@@]2(C)CCC[C@@]1(C)OC(=O)CC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446724
PubChem CID:	44566223
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	=	16.0	ug.mL-1	PMID[564701]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[564701]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[564701]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[564701]

☑ 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 NPC473592 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	178
0.1-0.2	1180
0.2-0.3	5107
0.3-0.4	14866
0.4-0.5	9207
0.5-0.6	6156
0.6-0.7	4872
0.7-0.8	1098
0.8-0.85	29
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC474979
0.9487	High Similarity	NPC476101
0.9114	High Similarity	NPC474978
0.8353	Intermediate Similarity	NPC76333
0.8313	Intermediate Similarity	NPC142163
0.8293	Intermediate Similarity	NPC100906
0.8256	Intermediate Similarity	NPC73038
0.8235	Intermediate Similarity	NPC156981
0.8222	Intermediate Similarity	NPC184006
0.8222	Intermediate Similarity	NPC78580
0.8222	Intermediate Similarity	NPC23621
0.8193	Intermediate Similarity	NPC37038
0.8171	Intermediate Similarity	NPC321514
0.8161	Intermediate Similarity	NPC171722
0.8132	Intermediate Similarity	NPC23241
0.8132	Intermediate Similarity	NPC195715
0.8118	Intermediate Similarity	NPC52108
0.8118	Intermediate Similarity	NPC476927
0.8118	Intermediate Similarity	NPC474789
0.8095	Intermediate Similarity	NPC327002
0.8072	Intermediate Similarity	NPC231431
0.8049	Intermediate Similarity	NPC132542
0.8046	Intermediate Similarity	NPC474970
0.8046	Intermediate Similarity	NPC325594
0.8046	Intermediate Similarity	NPC262085
0.8025	Intermediate Similarity	NPC279666
0.8025	Intermediate Similarity	NPC192540
0.8	Intermediate Similarity	NPC324341
0.8	Intermediate Similarity	NPC471588
0.8	Intermediate Similarity	NPC966
0.8	Intermediate Similarity	NPC288833
0.8	Intermediate Similarity	NPC228784
0.8	Intermediate Similarity	NPC155120
0.8	Intermediate Similarity	NPC282616
0.8	Intermediate Similarity	NPC6255
0.7978	Intermediate Similarity	NPC474570
0.7978	Intermediate Similarity	NPC471342
0.7978	Intermediate Similarity	NPC59682
0.7978	Intermediate Similarity	NPC474700
0.7978	Intermediate Similarity	NPC469866
0.7976	Intermediate Similarity	NPC269791
0.7976	Intermediate Similarity	NPC104545
0.7957	Intermediate Similarity	NPC26413
0.7952	Intermediate Similarity	NPC260385
0.7952	Intermediate Similarity	NPC179028
0.7952	Intermediate Similarity	NPC280654
0.7952	Intermediate Similarity	NPC110094
0.7931	Intermediate Similarity	NPC191965
0.7931	Intermediate Similarity	NPC476602
0.7927	Intermediate Similarity	NPC69143
0.7912	Intermediate Similarity	NPC86368
0.7907	Intermediate Similarity	NPC477373
0.7901	Intermediate Similarity	NPC241854
0.7901	Intermediate Similarity	NPC103958
0.7901	Intermediate Similarity	NPC161923
0.7901	Intermediate Similarity	NPC283908
0.7901	Intermediate Similarity	NPC251970
0.7901	Intermediate Similarity	NPC183503
0.7901	Intermediate Similarity	NPC71152
0.7901	Intermediate Similarity	NPC476046
0.7889	Intermediate Similarity	NPC86372
0.7889	Intermediate Similarity	NPC474728
0.7889	Intermediate Similarity	NPC120840
0.7889	Intermediate Similarity	NPC113989
0.7889	Intermediate Similarity	NPC172361
0.7889	Intermediate Similarity	NPC471896
0.7882	Intermediate Similarity	NPC142244
0.7882	Intermediate Similarity	NPC278459
0.7872	Intermediate Similarity	NPC164349
0.7857	Intermediate Similarity	NPC199595
0.7857	Intermediate Similarity	NPC327674
0.7849	Intermediate Similarity	NPC98874
0.7849	Intermediate Similarity	NPC120708
0.7849	Intermediate Similarity	NPC132824
0.7849	Intermediate Similarity	NPC269492
0.7849	Intermediate Similarity	NPC327788
0.7841	Intermediate Similarity	NPC84121
0.7841	Intermediate Similarity	NPC137306
0.7841	Intermediate Similarity	NPC324063
0.7831	Intermediate Similarity	NPC107039
0.7831	Intermediate Similarity	NPC283619
0.7831	Intermediate Similarity	NPC471897
0.7831	Intermediate Similarity	NPC471899
0.7826	Intermediate Similarity	NPC148964
0.7826	Intermediate Similarity	NPC222047
0.7802	Intermediate Similarity	NPC77099
0.7802	Intermediate Similarity	NPC476417
0.7802	Intermediate Similarity	NPC60755
0.7802	Intermediate Similarity	NPC285184
0.7802	Intermediate Similarity	NPC470590
0.7792	Intermediate Similarity	NPC474768
0.7791	Intermediate Similarity	NPC2524
0.7791	Intermediate Similarity	NPC256112
0.7791	Intermediate Similarity	NPC15910
0.7791	Intermediate Similarity	NPC286786
0.7789	Intermediate Similarity	NPC473576
0.7789	Intermediate Similarity	NPC475156
0.7778	Intermediate Similarity	NPC30522
0.7778	Intermediate Similarity	NPC270768
0.7778	Intermediate Similarity	NPC263393
0.7778	Intermediate Similarity	NPC61543
0.7778	Intermediate Similarity	NPC16265
0.7778	Intermediate Similarity	NPC130520
0.7778	Intermediate Similarity	NPC475921
0.7778	Intermediate Similarity	NPC121798
0.7778	Intermediate Similarity	NPC127689
0.7778	Intermediate Similarity	NPC225585
0.7778	Intermediate Similarity	NPC474704
0.7778	Intermediate Similarity	NPC234346
0.7778	Intermediate Similarity	NPC293048
0.7778	Intermediate Similarity	NPC59263
0.7766	Intermediate Similarity	NPC473456
0.7766	Intermediate Similarity	NPC89225
0.7765	Intermediate Similarity	NPC477057
0.7753	Intermediate Similarity	NPC166857
0.7753	Intermediate Similarity	NPC173089
0.7753	Intermediate Similarity	NPC158141
0.7753	Intermediate Similarity	NPC96496
0.7742	Intermediate Similarity	NPC148523
0.7727	Intermediate Similarity	NPC164424
0.7722	Intermediate Similarity	NPC94192
0.7717	Intermediate Similarity	NPC298554
0.7717	Intermediate Similarity	NPC38232
0.7717	Intermediate Similarity	NPC118490
0.7717	Intermediate Similarity	NPC131840
0.7711	Intermediate Similarity	NPC104806
0.7711	Intermediate Similarity	NPC89294
0.7708	Intermediate Similarity	NPC476888
0.7708	Intermediate Similarity	NPC93744
0.7701	Intermediate Similarity	NPC200752
0.7701	Intermediate Similarity	NPC132386
0.7701	Intermediate Similarity	NPC476100
0.7692	Intermediate Similarity	NPC148414
0.7692	Intermediate Similarity	NPC470589
0.7692	Intermediate Similarity	NPC126369
0.7692	Intermediate Similarity	NPC111110
0.7692	Intermediate Similarity	NPC175628
0.7692	Intermediate Similarity	NPC111585
0.7692	Intermediate Similarity	NPC130278
0.7684	Intermediate Similarity	NPC174663
0.7683	Intermediate Similarity	NPC91858
0.7683	Intermediate Similarity	NPC166797
0.7674	Intermediate Similarity	NPC267691
0.7674	Intermediate Similarity	NPC274050
0.7674	Intermediate Similarity	NPC48673
0.7674	Intermediate Similarity	NPC20096
0.7674	Intermediate Similarity	NPC471898
0.7674	Intermediate Similarity	NPC195334
0.7674	Intermediate Similarity	NPC162632
0.7674	Intermediate Similarity	NPC290495
0.7674	Intermediate Similarity	NPC263272
0.7674	Intermediate Similarity	NPC147066
0.7674	Intermediate Similarity	NPC221647
0.7674	Intermediate Similarity	NPC170303
0.7667	Intermediate Similarity	NPC52169
0.7667	Intermediate Similarity	NPC246708
0.7667	Intermediate Similarity	NPC48107
0.7667	Intermediate Similarity	NPC1753
0.7667	Intermediate Similarity	NPC474511
0.7667	Intermediate Similarity	NPC40552
0.7667	Intermediate Similarity	NPC182797
0.766	Intermediate Similarity	NPC327179
0.766	Intermediate Similarity	NPC472806
0.766	Intermediate Similarity	NPC201657
0.766	Intermediate Similarity	NPC167193
0.766	Intermediate Similarity	NPC471153
0.7654	Intermediate Similarity	NPC160817
0.7647	Intermediate Similarity	NPC16394
0.7647	Intermediate Similarity	NPC476438
0.7647	Intermediate Similarity	NPC192999
0.764	Intermediate Similarity	NPC322159
0.764	Intermediate Similarity	NPC475753
0.764	Intermediate Similarity	NPC476104
0.764	Intermediate Similarity	NPC82979
0.7634	Intermediate Similarity	NPC191412
0.7634	Intermediate Similarity	NPC114159
0.7634	Intermediate Similarity	NPC6818
0.7634	Intermediate Similarity	NPC159410
0.7634	Intermediate Similarity	NPC74751
0.7634	Intermediate Similarity	NPC215700
0.7634	Intermediate Similarity	NPC474529
0.7634	Intermediate Similarity	NPC296164
0.7634	Intermediate Similarity	NPC474963
0.7634	Intermediate Similarity	NPC80365
0.7634	Intermediate Similarity	NPC209868
0.7629	Intermediate Similarity	NPC40918
0.7629	Intermediate Similarity	NPC476890
0.7625	Intermediate Similarity	NPC476431
0.7619	Intermediate Similarity	NPC165711
0.7614	Intermediate Similarity	NPC96095
0.7614	Intermediate Similarity	NPC306951
0.7609	Intermediate Similarity	NPC177641
0.7609	Intermediate Similarity	NPC477574
0.7609	Intermediate Similarity	NPC36491
0.7609	Intermediate Similarity	NPC26888
0.7604	Intermediate Similarity	NPC35751
0.7604	Intermediate Similarity	NPC35239
0.759	Intermediate Similarity	NPC476844
0.7586	Intermediate Similarity	NPC69101
0.7586	Intermediate Similarity	NPC251779

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 NPC473592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1447
0.2-0.3	4025
0.3-0.4	2391
0.4-0.5	693
0.5-0.6	201
0.6-0.7	202
0.7-0.8	30
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
0.7634	Intermediate Similarity	NPD7748	Approved
0.7609	Intermediate Similarity	NPD6411	Approved
0.7556	Intermediate Similarity	NPD3573	Approved
0.7444	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7645	Phase 2
0.7419	Intermediate Similarity	NPD7515	Phase 2
0.7396	Intermediate Similarity	NPD6084	Phase 2
0.7396	Intermediate Similarity	NPD6083	Phase 2
0.7396	Intermediate Similarity	NPD7902	Approved
0.7391	Intermediate Similarity	NPD6101	Approved
0.7391	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6399	Phase 3
0.7262	Intermediate Similarity	NPD4784	Approved
0.7262	Intermediate Similarity	NPD4785	Approved
0.7255	Intermediate Similarity	NPD6899	Approved
0.7255	Intermediate Similarity	NPD6881	Approved
0.7253	Intermediate Similarity	NPD6098	Approved
0.7241	Intermediate Similarity	NPD4195	Approved
0.7229	Intermediate Similarity	NPD4243	Approved
0.7228	Intermediate Similarity	NPD6402	Approved
0.7228	Intermediate Similarity	NPD5739	Approved
0.7228	Intermediate Similarity	NPD7128	Approved
0.7228	Intermediate Similarity	NPD6675	Approved
0.7204	Intermediate Similarity	NPD6904	Approved
0.7204	Intermediate Similarity	NPD6673	Approved
0.7204	Intermediate Similarity	NPD6080	Approved
0.7188	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5695	Phase 3
0.7159	Intermediate Similarity	NPD7525	Registered
0.7157	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD4225	Approved
0.7115	Intermediate Similarity	NPD7290	Approved
0.7115	Intermediate Similarity	NPD6883	Approved
0.7115	Intermediate Similarity	NPD7102	Approved
0.7097	Intermediate Similarity	NPD5737	Approved
0.7097	Intermediate Similarity	NPD6672	Approved
0.7087	Intermediate Similarity	NPD7320	Approved
0.7083	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7900	Approved
0.7071	Intermediate Similarity	NPD7639	Approved
0.7071	Intermediate Similarity	NPD7640	Approved
0.7065	Intermediate Similarity	NPD6684	Approved
0.7065	Intermediate Similarity	NPD7521	Approved
0.7065	Intermediate Similarity	NPD7334	Approved
0.7065	Intermediate Similarity	NPD6409	Approved
0.7065	Intermediate Similarity	NPD7146	Approved
0.7065	Intermediate Similarity	NPD5330	Approved
0.7053	Intermediate Similarity	NPD5284	Approved
0.7053	Intermediate Similarity	NPD7637	Suspended
0.7053	Intermediate Similarity	NPD5281	Approved
0.7048	Intermediate Similarity	NPD6869	Approved
0.7048	Intermediate Similarity	NPD6650	Approved
0.7048	Intermediate Similarity	NPD6847	Approved
0.7048	Intermediate Similarity	NPD6649	Approved
0.7048	Intermediate Similarity	NPD8130	Phase 1
0.7048	Intermediate Similarity	NPD6617	Approved
0.7037	Intermediate Similarity	NPD7115	Discovery
0.7021	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6051	Approved
0.7019	Intermediate Similarity	NPD6012	Approved
0.7019	Intermediate Similarity	NPD6373	Approved
0.7019	Intermediate Similarity	NPD6372	Approved
0.7019	Intermediate Similarity	NPD6013	Approved
0.7019	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD4221	Approved
0.7	Intermediate Similarity	NPD4223	Phase 3
0.699	Remote Similarity	NPD5701	Approved
0.6981	Remote Similarity	NPD8297	Approved
0.6981	Remote Similarity	NPD6882	Approved
0.6979	Remote Similarity	NPD5779	Approved
0.6979	Remote Similarity	NPD5778	Approved
0.6966	Remote Similarity	NPD4695	Discontinued
0.6957	Remote Similarity	NPD5329	Approved
0.6923	Remote Similarity	NPD6011	Approved
0.6915	Remote Similarity	NPD5208	Approved
0.6915	Remote Similarity	NPD6903	Approved
0.6915	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6001	Approved
0.6882	Remote Similarity	NPD4623	Approved
0.6882	Remote Similarity	NPD3618	Phase 1
0.6882	Remote Similarity	NPD4519	Discontinued
0.6875	Remote Similarity	NPD6079	Approved
0.6875	Remote Similarity	NPD5693	Phase 1
0.6875	Remote Similarity	NPD6050	Approved
0.6875	Remote Similarity	NPD8035	Phase 2
0.6875	Remote Similarity	NPD8034	Phase 2
0.6875	Remote Similarity	NPD5694	Approved
0.6848	Remote Similarity	NPD4786	Approved
0.6848	Remote Similarity	NPD4197	Approved
0.6842	Remote Similarity	NPD4753	Phase 2
0.6842	Remote Similarity	NPD5328	Approved
0.6813	Remote Similarity	NPD3667	Approved
0.6782	Remote Similarity	NPD5275	Approved
0.6782	Remote Similarity	NPD4190	Phase 3
0.6782	Remote Similarity	NPD7339	Approved
0.6782	Remote Similarity	NPD6942	Approved
0.6774	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5207	Approved
0.6771	Remote Similarity	NPD5692	Phase 3
0.6733	Remote Similarity	NPD5285	Approved
0.6733	Remote Similarity	NPD5286	Approved
0.6733	Remote Similarity	NPD4696	Approved
0.6729	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4693	Phase 3
0.6702	Remote Similarity	NPD4138	Approved
0.6702	Remote Similarity	NPD4688	Approved
0.6702	Remote Similarity	NPD4690	Approved
0.6702	Remote Similarity	NPD5690	Phase 2
0.6702	Remote Similarity	NPD4689	Approved
0.6702	Remote Similarity	NPD5205	Approved
0.67	Remote Similarity	NPD4755	Approved
0.6696	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD5210	Approved
0.6633	Remote Similarity	NPD4202	Approved
0.663	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7492	Approved
0.6607	Remote Similarity	NPD7101	Approved
0.6607	Remote Similarity	NPD7100	Approved
0.6604	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5225	Approved
0.6602	Remote Similarity	NPD5224	Approved
0.6602	Remote Similarity	NPD5211	Phase 2
0.6602	Remote Similarity	NPD5226	Approved
0.6602	Remote Similarity	NPD4633	Approved
0.66	Remote Similarity	NPD5221	Approved
0.66	Remote Similarity	NPD5222	Approved
0.66	Remote Similarity	NPD7614	Phase 1
0.66	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4700	Approved
0.6566	Remote Similarity	NPD5707	Approved
0.6559	Remote Similarity	NPD6695	Phase 3
0.6556	Remote Similarity	NPD3617	Approved
0.6552	Remote Similarity	NPD6616	Approved
0.6549	Remote Similarity	NPD6054	Approved
0.6538	Remote Similarity	NPD5174	Approved
0.6538	Remote Similarity	NPD5175	Approved
0.6535	Remote Similarity	NPD5173	Approved
0.6526	Remote Similarity	NPD5280	Approved
0.6526	Remote Similarity	NPD4694	Approved
0.6518	Remote Similarity	NPD6335	Approved
0.6505	Remote Similarity	NPD5223	Approved
0.6496	Remote Similarity	NPD7078	Approved
0.6489	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3668	Phase 3
0.6486	Remote Similarity	NPD6274	Approved
0.6486	Remote Similarity	NPD6868	Approved
0.6481	Remote Similarity	NPD4634	Approved
0.6477	Remote Similarity	NPD6924	Approved
0.6477	Remote Similarity	NPD6926	Approved
0.6476	Remote Similarity	NPD5141	Approved
0.6455	Remote Similarity	NPD4632	Approved
0.6442	Remote Similarity	NPD7632	Discontinued
0.6441	Remote Similarity	NPD7736	Approved
0.6436	Remote Similarity	NPD4697	Phase 3
0.6435	Remote Similarity	NPD6370	Approved
0.6429	Remote Similarity	NPD6317	Approved
0.6421	Remote Similarity	NPD1694	Approved
0.6415	Remote Similarity	NPD6008	Approved
0.6404	Remote Similarity	NPD6059	Approved
0.6389	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6052	Approved
0.6379	Remote Similarity	NPD8328	Phase 3
0.6372	Remote Similarity	NPD6313	Approved
0.6372	Remote Similarity	NPD6314	Approved
0.6356	Remote Similarity	NPD8293	Discontinued
0.6355	Remote Similarity	NPD6614	Approved
0.6355	Remote Similarity	NPD6412	Phase 2
0.6348	Remote Similarity	NPD6909	Approved
0.6348	Remote Similarity	NPD6908	Approved
0.6348	Remote Similarity	NPD6015	Approved
0.6348	Remote Similarity	NPD7503	Approved
0.6348	Remote Similarity	NPD6016	Approved
0.6344	Remote Similarity	NPD4139	Approved
0.6344	Remote Similarity	NPD4692	Approved
0.6344	Remote Similarity	NPD5369	Approved
0.6337	Remote Similarity	NPD5654	Approved
0.6333	Remote Similarity	NPD6933	Approved
0.633	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6686	Approved
0.6296	Remote Similarity	NPD4729	Approved
0.6296	Remote Similarity	NPD4730	Approved
0.6293	Remote Similarity	NPD5988	Approved
0.6289	Remote Similarity	NPD7750	Discontinued
0.6289	Remote Similarity	NPD7524	Approved
0.6283	Remote Similarity	NPD6009	Approved
0.6283	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7732	Phase 3
0.6264	Remote Similarity	NPD6932	Approved
0.6262	Remote Similarity	NPD4767	Approved
0.6262	Remote Similarity	NPD4768	Approved
0.6239	Remote Similarity	NPD7604	Phase 2
0.6237	Remote Similarity	NPD6930	Phase 2

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