NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	402.23
Volume:	428.032
LogP:	4.748
LogD:	4.134
LogS:	-5.938
# Rotatable Bonds:	1
TPSA:	72.34
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	5.257
Fsp3:	0.577
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:	-4.89
MDCK Permeability:	2.3553944629384205e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.186
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.692

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.902
Plasma Protein Binding (PPB):	93.06749725341797%
Volume Distribution (VD):	2.147
Pgp-substrate:	4.513556003570557%

ADMET: Metabolism

CYP1A2-inhibitor:	0.288
CYP1A2-substrate:	0.892
CYP2C19-inhibitor:	0.665
CYP2C19-substrate:	0.715
CYP2C9-inhibitor:	0.899
CYP2C9-substrate:	0.328
CYP2D6-inhibitor:	0.716
CYP2D6-substrate:	0.336
CYP3A4-inhibitor:	0.837
CYP3A4-substrate:	0.894

ADMET: Excretion

Clearance (CL):	2.906
Half-life (T1/2):	0.385

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.054
Drug-inuced Liver Injury (DILI):	0.354
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.788
Carcinogencity:	0.417
Eye Corrosion:	0.077
Eye Irritation:	0.943
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC477135

Natural Product ID:	NPC477135
*Common Name:**	(1R,4R,5R,6R,8S,19R)-4-ethenyl-19-hydroxy-4,9,9,20,20-pentamethyl-7-oxa-11-azahexacyclo[14.3.1.05,19.06,8.010,18.012,17]icosa-10(18),12,14,16-tetraene-5-carbonitrile
IUPAC Name:	(1R,4R,5R,6R,8S,19R)-4-ethenyl-19-hydroxy-4,9,9,20,20-pentamethyl-7-oxa-11-azahexacyclo[14.3.1.05,19.06,8.010,18.012,17]icosa-10(18),12,14,16-tetraene-5-carbonitrile
Synonyms:	Ambiguine I Isonitrile
Standard InCHIKey:	AIZZJVVOSLWDHD-ZWCWJZTQSA-N
Standard InCHI:	InChI=1S/C26H30N2O2/c1-7-24(6)12-11-16-22(2,3)14-9-8-10-15-17(14)18-19(28-15)23(4,5)20-21(30-20)25(24,13-27)26(16,18)29/h7-10,16,20-21,28-29H,1,11-12H2,2-6H3/t16-,20-,21+,24+,25-,26-/m1/s1
SMILES:	C[C@@]1(CC[C@H]2[C@@]3([C@@]1([C@@H]4[C@@H](O4)C(C5=C3C6=C(C2(C)C)C=CC=C6N5)(C)C)C#N)O)C=C
Synthetic Gene Cluster:	BGC0001126;
ChEMBL Identifier:	n.a.
PubChem CID:	44419569
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO33609	Fischerella sp.	Species	Hapalosiphonaceae	Bacteria	n.a.	The Cactus Nursery, Herzliya, Israel	1996-JUL	PMID[17315959]

☑ 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
MIC	10

Activity Type	# Activity
Cell Line	1
Organism	9
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	128000	nM	PMID[19371071]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2.5	ug/ml	PMID[17315959]
NPT2	Others	Unspecified		MIC	=	0.078	ug/ml	PMID[17315959]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.312	ug/ml	PMID[17315959]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	0.312	ug/ml	PMID[17315959]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.39	ug/ml	PMID[17315959]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	13100	nM	PMID[19371071]
NPT1550	Organism	Bacillus anthracis	Bacillus anthracis	MIC	>	128000	nM	PMID[19371071]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8900	nM	PMID[19371071]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	59700	nM	PMID[19371071]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	1700	nM	PMID[19371071]

☑ 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 NPC477135 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	444
0.1-0.2	1689
0.2-0.3	6657
0.3-0.4	19006
0.4-0.5	10257
0.5-0.6	2913
0.6-0.7	1475
0.7-0.8	240
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9081	High Similarity	NPC205403
0.8696	High Similarity	NPC476319
0.8571	High Similarity	NPC61637
0.8163	Intermediate Similarity	NPC476175
0.8138	Intermediate Similarity	NPC302191
0.8103	Intermediate Similarity	NPC231342
0.8095	Intermediate Similarity	NPC19679
0.8085	Intermediate Similarity	NPC198339
0.8009	Intermediate Similarity	NPC112547
0.7946	Intermediate Similarity	NPC154293
0.7927	Intermediate Similarity	NPC119700
0.7889	Intermediate Similarity	NPC32200
0.7887	Intermediate Similarity	NPC34271
0.7865	Intermediate Similarity	NPC165201
0.7819	Intermediate Similarity	NPC97525
0.7799	Intermediate Similarity	NPC314552
0.7795	Intermediate Similarity	NPC128751
0.7755	Intermediate Similarity	NPC469497
0.7755	Intermediate Similarity	NPC106833
0.7749	Intermediate Similarity	NPC6093
0.7749	Intermediate Similarity	NPC472443
0.7721	Intermediate Similarity	NPC249342
0.772	Intermediate Similarity	NPC472444
0.7704	Intermediate Similarity	NPC246700
0.77	Intermediate Similarity	NPC153042
0.7692	Intermediate Similarity	NPC235900
0.7692	Intermediate Similarity	NPC475778
0.7665	Intermediate Similarity	NPC206967
0.7665	Intermediate Similarity	NPC95783
0.7639	Intermediate Similarity	NPC470873
0.7632	Intermediate Similarity	NPC34508
0.7629	Intermediate Similarity	NPC472108
0.7629	Intermediate Similarity	NPC139291
0.7619	Intermediate Similarity	NPC471284
0.7617	Intermediate Similarity	NPC300688
0.7606	Intermediate Similarity	NPC61813
0.76	Intermediate Similarity	NPC85066
0.76	Intermediate Similarity	NPC181502
0.7596	Intermediate Similarity	NPC234999
0.7574	Intermediate Similarity	NPC473747
0.7573	Intermediate Similarity	NPC476106
0.7569	Intermediate Similarity	NPC477134
0.7565	Intermediate Similarity	NPC270009
0.756	Intermediate Similarity	NPC250129
0.7547	Intermediate Similarity	NPC96131
0.7536	Intermediate Similarity	NPC473650
0.7536	Intermediate Similarity	NPC193777
0.7536	Intermediate Similarity	NPC160527
0.7526	Intermediate Similarity	NPC280548
0.7524	Intermediate Similarity	NPC48353
0.7523	Intermediate Similarity	NPC470874
0.7513	Intermediate Similarity	NPC151939
0.7512	Intermediate Similarity	NPC475165
0.75	Intermediate Similarity	NPC189812
0.75	Intermediate Similarity	NPC472586
0.75	Intermediate Similarity	NPC475151
0.75	Intermediate Similarity	NPC190007
0.75	Intermediate Similarity	NPC329688
0.7488	Intermediate Similarity	NPC18661
0.7487	Intermediate Similarity	NPC314394
0.7477	Intermediate Similarity	NPC57690
0.7467	Intermediate Similarity	NPC470843
0.7467	Intermediate Similarity	NPC94541
0.7462	Intermediate Similarity	NPC94943
0.7462	Intermediate Similarity	NPC473189
0.7453	Intermediate Similarity	NPC97388
0.7437	Intermediate Similarity	NPC46413
0.7427	Intermediate Similarity	NPC123019
0.7426	Intermediate Similarity	NPC195314
0.7424	Intermediate Similarity	NPC99428
0.7423	Intermediate Similarity	NPC293472
0.7419	Intermediate Similarity	NPC285469
0.7406	Intermediate Similarity	NPC473547
0.7398	Intermediate Similarity	NPC192270
0.7395	Intermediate Similarity	NPC475476
0.7395	Intermediate Similarity	NPC242446
0.7385	Intermediate Similarity	NPC88363
0.7379	Intermediate Similarity	NPC267423
0.7364	Intermediate Similarity	NPC252251
0.736	Intermediate Similarity	NPC212535
0.736	Intermediate Similarity	NPC472110
0.736	Intermediate Similarity	NPC472109
0.7358	Intermediate Similarity	NPC313791
0.7358	Intermediate Similarity	NPC474409
0.7354	Intermediate Similarity	NPC16667
0.7353	Intermediate Similarity	NPC70956
0.7353	Intermediate Similarity	NPC243834
0.7343	Intermediate Similarity	NPC475085
0.7343	Intermediate Similarity	NPC162730
0.7343	Intermediate Similarity	NPC291535
0.7343	Intermediate Similarity	NPC475112
0.7343	Intermediate Similarity	NPC474116
0.7339	Intermediate Similarity	NPC266192
0.733	Intermediate Similarity	NPC249040
0.7326	Intermediate Similarity	NPC141353
0.7326	Intermediate Similarity	NPC184476
0.7324	Intermediate Similarity	NPC478074
0.7321	Intermediate Similarity	NPC187456
0.7309	Intermediate Similarity	NPC70155
0.7306	Intermediate Similarity	NPC126492
0.7299	Intermediate Similarity	NPC201697
0.7297	Intermediate Similarity	NPC477531
0.7297	Intermediate Similarity	NPC282033
0.7296	Intermediate Similarity	NPC72980
0.7292	Intermediate Similarity	NPC317430
0.7277	Intermediate Similarity	NPC470508
0.7273	Intermediate Similarity	NPC79107
0.7273	Intermediate Similarity	NPC475424
0.7273	Intermediate Similarity	NPC470507
0.7273	Intermediate Similarity	NPC207726
0.7273	Intermediate Similarity	NPC471458
0.7273	Intermediate Similarity	NPC267926
0.7264	Intermediate Similarity	NPC475422
0.7256	Intermediate Similarity	NPC469928
0.7256	Intermediate Similarity	NPC251936
0.7252	Intermediate Similarity	NPC473806
0.7252	Intermediate Similarity	NPC471634
0.7252	Intermediate Similarity	NPC209174
0.7246	Intermediate Similarity	NPC195461
0.7246	Intermediate Similarity	NPC313985
0.7246	Intermediate Similarity	NPC81654
0.7246	Intermediate Similarity	NPC79129
0.7246	Intermediate Similarity	NPC249150
0.7246	Intermediate Similarity	NPC49196
0.7233	Intermediate Similarity	NPC72211
0.723	Intermediate Similarity	NPC9894
0.7227	Intermediate Similarity	NPC313884
0.7227	Intermediate Similarity	NPC98371
0.7225	Intermediate Similarity	NPC162484
0.7225	Intermediate Similarity	NPC223427
0.7213	Intermediate Similarity	NPC242556
0.7211	Intermediate Similarity	NPC473320
0.7208	Intermediate Similarity	NPC176199
0.7208	Intermediate Similarity	NPC215795
0.7202	Intermediate Similarity	NPC86078
0.7202	Intermediate Similarity	NPC201700
0.7196	Intermediate Similarity	NPC294620
0.7194	Intermediate Similarity	NPC472122
0.7194	Intermediate Similarity	NPC24594
0.7183	Intermediate Similarity	NPC11464
0.7179	Intermediate Similarity	NPC472123
0.7176	Intermediate Similarity	NPC203614
0.7176	Intermediate Similarity	NPC330009
0.7176	Intermediate Similarity	NPC204491
0.7171	Intermediate Similarity	NPC205934
0.7171	Intermediate Similarity	NPC43787
0.717	Intermediate Similarity	NPC475910
0.717	Intermediate Similarity	NPC87755
0.7169	Intermediate Similarity	NPC477532
0.7162	Intermediate Similarity	NPC470126
0.7158	Intermediate Similarity	NPC67056
0.7157	Intermediate Similarity	NPC99666
0.7157	Intermediate Similarity	NPC55493
0.7151	Intermediate Similarity	NPC124005
0.7151	Intermediate Similarity	NPC37548
0.715	Intermediate Similarity	NPC50503
0.7149	Intermediate Similarity	NPC141428
0.7143	Intermediate Similarity	NPC469470
0.7143	Intermediate Similarity	NPC290529
0.7143	Intermediate Similarity	NPC469501
0.7136	Intermediate Similarity	NPC70259
0.7136	Intermediate Similarity	NPC284102
0.7135	Intermediate Similarity	NPC311276
0.7135	Intermediate Similarity	NPC102423
0.7135	Intermediate Similarity	NPC162799
0.7135	Intermediate Similarity	NPC472587
0.713	Intermediate Similarity	NPC253580
0.7128	Intermediate Similarity	NPC158129
0.712	Intermediate Similarity	NPC131718
0.7115	Intermediate Similarity	NPC128823
0.7115	Intermediate Similarity	NPC241024
0.7114	Intermediate Similarity	NPC62510
0.7112	Intermediate Similarity	NPC473389
0.7111	Intermediate Similarity	NPC475720
0.7111	Intermediate Similarity	NPC474192
0.711	Intermediate Similarity	NPC469594
0.7107	Intermediate Similarity	NPC56618
0.7107	Intermediate Similarity	NPC288785
0.7105	Intermediate Similarity	NPC11408
0.7103	Intermediate Similarity	NPC126066
0.7091	Intermediate Similarity	NPC471506
0.709	Intermediate Similarity	NPC38736
0.7087	Intermediate Similarity	NPC131017
0.7085	Intermediate Similarity	NPC472105
0.7085	Intermediate Similarity	NPC187827
0.7081	Intermediate Similarity	NPC329747
0.7081	Intermediate Similarity	NPC214428
0.7072	Intermediate Similarity	NPC235885
0.7071	Intermediate Similarity	NPC211997
0.7071	Intermediate Similarity	NPC326575
0.7071	Intermediate Similarity	NPC68354
0.707	Intermediate Similarity	NPC204303
0.7069	Intermediate Similarity	NPC199259
0.7059	Intermediate Similarity	NPC187951
0.7059	Intermediate Similarity	NPC41318
0.7059	Intermediate Similarity	NPC329858
0.7059	Intermediate Similarity	NPC469312
0.7056	Intermediate Similarity	NPC275305
0.7056	Intermediate Similarity	NPC37423
0.7056	Intermediate Similarity	NPC469743

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 NPC477135 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	577
0.2-0.3	661
0.3-0.4	1947
0.4-0.5	3334
0.5-0.6	1868
0.6-0.7	459
0.7-0.8	37
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
0.7799	Intermediate Similarity	NPD5164	Discontinued
0.7647	Intermediate Similarity	NPD2920	Discontinued
0.7619	Intermediate Similarity	NPD1325	Approved
0.7619	Intermediate Similarity	NPD1326	Approved
0.7538	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD5913	Phase 3
0.7525	Intermediate Similarity	NPD5003	Discontinued
0.7391	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7418	Discontinued
0.7254	Intermediate Similarity	NPD7474	Suspended
0.7246	Intermediate Similarity	NPD4601	Approved
0.7246	Intermediate Similarity	NPD4600	Approved
0.723	Intermediate Similarity	NPD5936	Approved
0.723	Intermediate Similarity	NPD5939	Approved
0.7228	Intermediate Similarity	NPD2565	Phase 2
0.7228	Intermediate Similarity	NPD2564	Approved
0.7227	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD2177	Approved
0.7198	Intermediate Similarity	NPD2175	Phase 3
0.7198	Intermediate Similarity	NPD2176	Approved
0.7186	Intermediate Similarity	NPD5596	Phase 2
0.7177	Intermediate Similarity	NPD6975	Discontinued
0.7162	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6978	Phase 2
0.7156	Intermediate Similarity	NPD6455	Phase 3
0.7129	Intermediate Similarity	NPD4511	Phase 1
0.7129	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6290	Phase 2
0.7123	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4079	Approved
0.7121	Intermediate Similarity	NPD4076	Approved
0.7115	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6985	Discontinued
0.7104	Intermediate Similarity	NPD1592	Phase 3
0.7095	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3003	Approved
0.7074	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6158	Phase 2
0.7071	Intermediate Similarity	NPD3506	Approved
0.7071	Intermediate Similarity	NPD3505	Approved
0.7056	Intermediate Similarity	NPD5065	Approved
0.7047	Intermediate Similarity	NPD5138	Approved
0.7047	Intermediate Similarity	NPD5140	Approved
0.7039	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD2844	Phase 3
0.7021	Intermediate Similarity	NPD4463	Approved
0.7021	Intermediate Similarity	NPD4462	Approved
0.702	Intermediate Similarity	NPD2380	Approved
0.702	Intermediate Similarity	NPD2382	Approved
0.702	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2381	Approved
0.7019	Intermediate Similarity	NPD7948	Phase 1
0.7015	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD2916	Discontinued
0.7009	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7194	Discontinued
0.6995	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD4502	Phase 2
0.6986	Remote Similarity	NPD7777	Approved
0.6986	Remote Similarity	NPD7778	Approved
0.6986	Remote Similarity	NPD53	Approved
0.6976	Remote Similarity	NPD6281	Approved
0.6976	Remote Similarity	NPD4499	Approved
0.6972	Remote Similarity	NPD5902	Approved
0.6972	Remote Similarity	NPD5903	Approved
0.6961	Remote Similarity	NPD8431	Approved
0.6959	Remote Similarity	NPD3330	Phase 1
0.6955	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5021	Discontinued
0.6935	Remote Similarity	NPD5100	Phase 3
0.6919	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7957	Phase 1
0.6916	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5067	Phase 2
0.6912	Remote Similarity	NPD5066	Phase 2
0.6912	Remote Similarity	NPD6220	Phase 3
0.6907	Remote Similarity	NPD1684	Approved
0.6907	Remote Similarity	NPD1685	Approved
0.6906	Remote Similarity	NPD6995	Phase 1
0.6905	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD2882	Phase 1
0.689	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7453	Approved
0.6884	Remote Similarity	NPD6492	Phase 2
0.6884	Remote Similarity	NPD7452	Approved
0.6878	Remote Similarity	NPD2383	Phase 1
0.6875	Remote Similarity	NPD1038	Approved
0.6872	Remote Similarity	NPD8395	Approved
0.6872	Remote Similarity	NPD1768	Approved
0.6872	Remote Similarity	NPD8396	Approved
0.6866	Remote Similarity	NPD8386	Phase 2
0.6856	Remote Similarity	NPD7558	Phase 2
0.6852	Remote Similarity	NPD5658	Approved
0.6845	Remote Similarity	NPD5254	Discontinued
0.6842	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD6145	Phase 1
0.6806	Remote Similarity	NPD7222	Phase 2
0.6792	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5425	Phase 1
0.6791	Remote Similarity	NPD3525	Discontinued
0.6787	Remote Similarity	NPD5612	Discontinued
0.6783	Remote Similarity	NPD6494	Phase 2
0.678	Remote Similarity	NPD6227	Discontinued
0.6776	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD8094	Discontinued
0.6768	Remote Similarity	NPD4640	Approved
0.6768	Remote Similarity	NPD4638	Approved
0.6768	Remote Similarity	NPD4639	Approved
0.6761	Remote Similarity	NPD4501	Approved
0.6761	Remote Similarity	NPD4500	Approved
0.6759	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5530	Phase 1
0.6754	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD6452	Discontinued
0.6749	Remote Similarity	NPD6595	Phase 3
0.6746	Remote Similarity	NPD3404	Approved
0.6733	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6159	Phase 2
0.6732	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8093	Discontinued
0.6716	Remote Similarity	NPD4203	Approved
0.6716	Remote Similarity	NPD4204	Approved
0.6715	Remote Similarity	NPD4948	Discontinued
0.6714	Remote Similarity	NPD802	Phase 2
0.6714	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5901	Discontinued
0.6699	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7672	Approved
0.6697	Remote Similarity	NPD7671	Approved
0.6683	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD1534	Approved
0.6683	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4506	Discontinued
0.6667	Remote Similarity	NPD6176	Phase 1
0.6667	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7878	Phase 2
0.6651	Remote Similarity	NPD1392	Approved
0.6651	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD3814	Phase 1
0.6634	Remote Similarity	NPD7867	Phase 1
0.6633	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6770	Approved
0.6618	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD3323	Discontinued
0.6614	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7470	Discontinued
0.6605	Remote Similarity	NPD6479	Discontinued
0.6604	Remote Similarity	NPD6590	Discontinued
0.6596	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4437	Phase 3
0.659	Remote Similarity	NPD6991	Approved
0.6589	Remote Similarity	NPD7946	Pre-registration
0.6589	Remote Similarity	NPD2727	Phase 2
0.6584	Remote Similarity	NPD43	Approved
0.6584	Remote Similarity	NPD6182	Approved
0.6584	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7770	Phase 3
0.6578	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2794	Discontinued
0.6571	Remote Similarity	NPD7956	Approved
0.6571	Remote Similarity	NPD7955	Approved
0.6569	Remote Similarity	NPD6641	Approved
0.6569	Remote Similarity	NPD4181	Approved
0.6569	Remote Similarity	NPD6642	Approved
0.6569	Remote Similarity	NPD2144	Approved
0.6568	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD8016	Phase 3
0.6562	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3013	Phase 3
0.6558	Remote Similarity	NPD3825	Phase 3
0.6553	Remote Similarity	NPD3038	Discontinued
0.6547	Remote Similarity	NPD7276	Approved
0.6547	Remote Similarity	NPD7277	Approved
0.6545	Remote Similarity	NPD6376	Discontinued
0.654	Remote Similarity	NPD7417	Discontinued
0.6537	Remote Similarity	NPD3920	Phase 2
0.6537	Remote Similarity	NPD3417	Phase 1
0.653	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD484	Approved
0.6528	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD1262	Discovery
0.6522	Remote Similarity	NPD2092	Phase 2
0.6522	Remote Similarity	NPD2095	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