NPASS Compound

Structure

NPC90415 OpenBabel07101719142D 23 25 0 0 0 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 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 -2.5981 0.5000 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 2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -1.7321 0.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 4 1 0 0 0 0 2 6 2 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 12 2 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 9 1 0 0 0 0 8 11 2 0 0 0 0 9 12 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 12 16 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 17 20 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.12
Volume:	318.851
LogP:	1.598
LogD:	1.662
LogS:	-3.208
# Rotatable Bonds:	4
TPSA:	83.31
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	2.589
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.967
MDCK Permeability:	1.3746773220191244e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	96.5818099975586%
Volume Distribution (VD):	0.4
Pgp-substrate:	1.6758368015289307%

ADMET: Metabolism

CYP1A2-inhibitor:	0.12
CYP1A2-substrate:	0.217
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.496
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.215
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	3.43
Half-life (T1/2):	0.756

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.922
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.206
Skin Sensitization:	0.123
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.169
Respiratory Toxicity:	0.712

Download Data

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

Natural Product: NPC90415

Natural Product ID:	NPC90415
*Common Name:**	9-[(E)-4-Hydroxy-3-Methylbut-2-Enyl]Phenazine-1-Carboxylic Acid
IUPAC Name:	9-[(E)-4-hydroxy-3-methylbut-2-enyl]phenazine-1-carboxylic acid
Synonyms:
Standard InCHIKey:	VJNPRSAWVPWWEV-DHZHZOJOSA-N
Standard InCHI:	InChI=1S/C18H16N2O3/c1-11(10-21)8-9-12-4-2-6-14-16(12)20-17-13(18(22)23)5-3-7-15(17)19-14/h2-8,21H,9-10H2,1H3,(H,22,23)/b11-8+
SMILES:	OC/C(=C/Cc1cccc2c1nc1c(n2)cccc1C(=O)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3233854
PubChem CID:	90670174
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000486] Quinoxalines [CHEMONTID:0000416] Phenazines and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33323	Kitasatospora sp. HKI 714	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24617951]

☑ 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	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	100.0	ug.mL-1	PMID[516691]
NPT1176	Organism	Mycobacterium fortuitum	Mycobacterium fortuitum	MIC	=	25.0	ug.mL-1	PMID[516691]
NPT5246	Organism	Mycobacterium aurum	Mycobacterium aurum	MIC	=	25.0	ug.mL-1	PMID[516691]
NPT3473	Organism	Mycobacterium vaccae	Mycobacterium vaccae	MIC	=	25.0	ug.mL-1	PMID[516691]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	50.0	ug.mL-1	PMID[516691]

☑ 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 NPC90415 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	286
0.1-0.2	2191
0.2-0.3	10554
0.3-0.4	12192
0.4-0.5	12795
0.5-0.6	2787
0.6-0.7	1712
0.7-0.8	151
0.8-0.85	11
0.85-0.9	9
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9818	High Similarity	NPC243058
0.9641	High Similarity	NPC203635
0.9576	High Similarity	NPC219848
0.9518	High Similarity	NPC256268
0.9116	High Similarity	NPC314648
0.8962	High Similarity	NPC314855
0.8962	High Similarity	NPC315638
0.8962	High Similarity	NPC313345
0.8962	High Similarity	NPC313796
0.8913	High Similarity	NPC315545
0.8913	High Similarity	NPC314297
0.877	High Similarity	NPC314834
0.8677	High Similarity	NPC244856
0.8534	High Similarity	NPC236424
0.8534	High Similarity	NPC306644
0.849	Intermediate Similarity	NPC274842
0.828	Intermediate Similarity	NPC474916
0.8204	Intermediate Similarity	NPC288445
0.8035	Intermediate Similarity	NPC322644
0.8035	Intermediate Similarity	NPC27904
0.7889	Intermediate Similarity	NPC84347
0.7889	Intermediate Similarity	NPC471743
0.7876	Intermediate Similarity	NPC165599
0.7838	Intermediate Similarity	NPC194040
0.7833	Intermediate Similarity	NPC303225
0.7826	Intermediate Similarity	NPC471742
0.7755	Intermediate Similarity	NPC244741
0.7753	Intermediate Similarity	NPC182131
0.7749	Intermediate Similarity	NPC141454
0.768	Intermediate Similarity	NPC471944
0.7673	Intermediate Similarity	NPC312645
0.7628	Intermediate Similarity	NPC291609
0.7612	Intermediate Similarity	NPC89508
0.7581	Intermediate Similarity	NPC124300
0.7551	Intermediate Similarity	NPC57398
0.7513	Intermediate Similarity	NPC278434
0.75	Intermediate Similarity	NPC282103
0.7487	Intermediate Similarity	NPC243850
0.7487	Intermediate Similarity	NPC470317
0.7486	Intermediate Similarity	NPC191310
0.7477	Intermediate Similarity	NPC310618
0.7475	Intermediate Similarity	NPC132539
0.7447	Intermediate Similarity	NPC207851
0.7438	Intermediate Similarity	NPC250448
0.7385	Intermediate Similarity	NPC90229
0.7382	Intermediate Similarity	NPC183805
0.7376	Intermediate Similarity	NPC123839
0.7368	Intermediate Similarity	NPC314573
0.7368	Intermediate Similarity	NPC229893
0.7366	Intermediate Similarity	NPC322064
0.7363	Intermediate Similarity	NPC266249
0.7363	Intermediate Similarity	NPC41717
0.7353	Intermediate Similarity	NPC31700
0.733	Intermediate Similarity	NPC206186
0.732	Intermediate Similarity	NPC230403
0.7317	Intermediate Similarity	NPC477979
0.7316	Intermediate Similarity	NPC476341
0.731	Intermediate Similarity	NPC81535
0.731	Intermediate Similarity	NPC280714
0.7306	Intermediate Similarity	NPC138370
0.7286	Intermediate Similarity	NPC328318
0.7286	Intermediate Similarity	NPC328596
0.7285	Intermediate Similarity	NPC218388
0.7263	Intermediate Similarity	NPC470003
0.7254	Intermediate Similarity	NPC313293
0.7254	Intermediate Similarity	NPC144381
0.7246	Intermediate Similarity	NPC27041
0.7231	Intermediate Similarity	NPC45850
0.7228	Intermediate Similarity	NPC470894
0.7209	Intermediate Similarity	NPC85443
0.7208	Intermediate Similarity	NPC474188
0.7202	Intermediate Similarity	NPC61435
0.7188	Intermediate Similarity	NPC160381
0.7172	Intermediate Similarity	NPC102008
0.7158	Intermediate Similarity	NPC314394
0.7158	Intermediate Similarity	NPC113626
0.7157	Intermediate Similarity	NPC472116
0.715	Intermediate Similarity	NPC472323
0.7128	Intermediate Similarity	NPC151635
0.7122	Intermediate Similarity	NPC309845
0.712	Intermediate Similarity	NPC471130
0.7113	Intermediate Similarity	NPC221873
0.7112	Intermediate Similarity	NPC252572
0.7105	Intermediate Similarity	NPC15840
0.7104	Intermediate Similarity	NPC88970
0.7101	Intermediate Similarity	NPC317752
0.7094	Intermediate Similarity	NPC317373
0.7092	Intermediate Similarity	NPC272458
0.7083	Intermediate Similarity	NPC472119
0.7079	Intermediate Similarity	NPC317572
0.7077	Intermediate Similarity	NPC324091
0.7071	Intermediate Similarity	NPC79356
0.7071	Intermediate Similarity	NPC102592
0.7059	Intermediate Similarity	NPC193238
0.7053	Intermediate Similarity	NPC318299
0.7053	Intermediate Similarity	NPC118940
0.7044	Intermediate Similarity	NPC472259
0.7044	Intermediate Similarity	NPC327592
0.7039	Intermediate Similarity	NPC227824
0.7037	Intermediate Similarity	NPC116622
0.7032	Intermediate Similarity	NPC57453
0.7031	Intermediate Similarity	NPC159125
0.7026	Intermediate Similarity	NPC175474
0.702	Intermediate Similarity	NPC202812
0.7016	Intermediate Similarity	NPC88110
0.7016	Intermediate Similarity	NPC24864
0.7016	Intermediate Similarity	NPC73994
0.701	Intermediate Similarity	NPC62749
0.7005	Intermediate Similarity	NPC67551
0.7005	Intermediate Similarity	NPC9894
0.7	Intermediate Similarity	NPC28848
0.7	Intermediate Similarity	NPC14325
0.6995	Remote Similarity	NPC46895
0.699	Remote Similarity	NPC154339
0.6986	Remote Similarity	NPC182222
0.6985	Remote Similarity	NPC245916
0.6984	Remote Similarity	NPC469938
0.6981	Remote Similarity	NPC323969
0.698	Remote Similarity	NPC470586
0.6976	Remote Similarity	NPC53344
0.6973	Remote Similarity	NPC189116
0.6972	Remote Similarity	NPC207686
0.697	Remote Similarity	NPC267343
0.6968	Remote Similarity	NPC273532
0.6968	Remote Similarity	NPC249614
0.6959	Remote Similarity	NPC133003
0.6954	Remote Similarity	NPC129909
0.6954	Remote Similarity	NPC114974
0.6943	Remote Similarity	NPC48938
0.6942	Remote Similarity	NPC470280
0.6942	Remote Similarity	NPC39679
0.6939	Remote Similarity	NPC63199
0.6939	Remote Similarity	NPC102338
0.6939	Remote Similarity	NPC196251
0.6939	Remote Similarity	NPC111602
0.6935	Remote Similarity	NPC135950
0.6935	Remote Similarity	NPC220151
0.6935	Remote Similarity	NPC19692
0.6932	Remote Similarity	NPC60553
0.6927	Remote Similarity	NPC237649
0.6927	Remote Similarity	NPC300596
0.6927	Remote Similarity	NPC475685
0.6927	Remote Similarity	NPC61011
0.6923	Remote Similarity	NPC263455
0.6919	Remote Similarity	NPC55493
0.6916	Remote Similarity	NPC478141
0.6915	Remote Similarity	NPC212213
0.6915	Remote Similarity	NPC52557
0.6911	Remote Similarity	NPC234987
0.691	Remote Similarity	NPC167400
0.6907	Remote Similarity	NPC285923
0.6906	Remote Similarity	NPC284348
0.6904	Remote Similarity	NPC329858
0.6904	Remote Similarity	NPC83111
0.6903	Remote Similarity	NPC107836
0.69	Remote Similarity	NPC109922
0.69	Remote Similarity	NPC128244
0.6898	Remote Similarity	NPC473506
0.6895	Remote Similarity	NPC132329
0.6881	Remote Similarity	NPC241024
0.6881	Remote Similarity	NPC472844
0.6878	Remote Similarity	NPC158129
0.6878	Remote Similarity	NPC477549
0.6875	Remote Similarity	NPC234999
0.6875	Remote Similarity	NPC303951
0.6875	Remote Similarity	NPC164340
0.6872	Remote Similarity	NPC62995
0.6872	Remote Similarity	NPC469928
0.6872	Remote Similarity	NPC478186
0.6868	Remote Similarity	NPC36168
0.686	Remote Similarity	NPC253476
0.6859	Remote Similarity	NPC150048
0.6859	Remote Similarity	NPC203754
0.6858	Remote Similarity	NPC178858
0.6857	Remote Similarity	NPC471741
0.6857	Remote Similarity	NPC151781
0.6857	Remote Similarity	NPC74562
0.6857	Remote Similarity	NPC316181
0.6856	Remote Similarity	NPC102755
0.6853	Remote Similarity	NPC44354
0.6852	Remote Similarity	NPC475498
0.6852	Remote Similarity	NPC475137
0.685	Remote Similarity	NPC276517
0.6848	Remote Similarity	NPC26850
0.6845	Remote Similarity	NPC82053
0.6845	Remote Similarity	NPC238457
0.6842	Remote Similarity	NPC23294
0.6842	Remote Similarity	NPC87413
0.684	Remote Similarity	NPC469727
0.6839	Remote Similarity	NPC471997
0.6837	Remote Similarity	NPC135601
0.6837	Remote Similarity	NPC220851
0.6837	Remote Similarity	NPC17273
0.6837	Remote Similarity	NPC141612
0.6835	Remote Similarity	NPC471977
0.6835	Remote Similarity	NPC470486
0.6835	Remote Similarity	NPC471190
0.6835	Remote Similarity	NPC475644
0.6833	Remote Similarity	NPC94428
0.6833	Remote Similarity	NPC263937

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 NPC90415 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	635
0.2-0.3	787
0.3-0.4	1459
0.4-0.5	2860
0.5-0.6	2334
0.6-0.7	792
0.7-0.8	68
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8202	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD4948	Discontinued
0.7689	Intermediate Similarity	NPD4938	Phase 2
0.7688	Intermediate Similarity	NPD2882	Phase 1
0.7688	Intermediate Similarity	NPD5416	Discontinued
0.763	Intermediate Similarity	NPD6142	Phase 3
0.7622	Intermediate Similarity	NPD7867	Phase 1
0.7552	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD3794	Approved
0.7525	Intermediate Similarity	NPD3795	Approved
0.7488	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6158	Phase 2
0.7486	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD6492	Phase 2
0.7426	Intermediate Similarity	NPD5475	Discontinued
0.7424	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5821	Approved
0.7391	Intermediate Similarity	NPD43	Approved
0.7391	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6182	Approved
0.7363	Intermediate Similarity	NPD2509	Approved
0.7363	Intermediate Similarity	NPD2510	Approved
0.7358	Intermediate Similarity	NPD4376	Phase 3
0.7343	Intermediate Similarity	NPD7404	Approved
0.7326	Intermediate Similarity	NPD1625	Approved
0.7314	Intermediate Similarity	NPD4888	Discontinued
0.7308	Intermediate Similarity	NPD3280	Approved
0.7306	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD2336	Approved
0.7304	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6733	Discontinued
0.7264	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD5488	Discontinued
0.7236	Intermediate Similarity	NPD7727	Phase 2
0.7233	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7767	Approved
0.7212	Intermediate Similarity	NPD7878	Phase 2
0.7208	Intermediate Similarity	NPD5003	Discontinued
0.7207	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4334	Discontinued
0.7188	Intermediate Similarity	NPD3315	Phase 3
0.7178	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD53	Approved
0.7172	Intermediate Similarity	NPD7778	Approved
0.7172	Intermediate Similarity	NPD7777	Approved
0.7168	Intermediate Similarity	NPD1189	Approved
0.7158	Intermediate Similarity	NPD1631	Approved
0.7157	Intermediate Similarity	NPD5512	Phase 3
0.7157	Intermediate Similarity	NPD2307	Discontinued
0.7151	Intermediate Similarity	NPD3776	Discontinued
0.715	Intermediate Similarity	NPD7817	Phase 1
0.7143	Intermediate Similarity	NPD5827	Discontinued
0.7136	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2844	Phase 3
0.7129	Intermediate Similarity	NPD5901	Discontinued
0.7129	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6987	Phase 1
0.7127	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3959	Phase 2
0.7117	Intermediate Similarity	NPD3962	Phase 2
0.7115	Intermediate Similarity	NPD3393	Approved
0.7115	Intermediate Similarity	NPD3394	Approved
0.7115	Intermediate Similarity	NPD3389	Approved
0.71	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1573	Approved
0.7097	Intermediate Similarity	NPD1575	Approved
0.7093	Intermediate Similarity	NPD1626	Approved
0.7085	Intermediate Similarity	NPD4397	Phase 1
0.7083	Intermediate Similarity	NPD5923	Phase 1
0.7077	Intermediate Similarity	NPD3321	Discontinued
0.7074	Intermediate Similarity	NPD4883	Approved
0.7073	Intermediate Similarity	NPD4506	Discontinued
0.7059	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6999	Discontinued
0.705	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7395	Discontinued
0.7047	Intermediate Similarity	NPD6227	Discontinued
0.7044	Intermediate Similarity	NPD3947	Discontinued
0.7044	Intermediate Similarity	NPD8115	Approved
0.7044	Intermediate Similarity	NPD8114	Approved
0.7044	Intermediate Similarity	NPD7103	Approved
0.7043	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5020	Approved
0.7016	Intermediate Similarity	NPD5899	Approved
0.7016	Intermediate Similarity	NPD5897	Approved
0.7016	Intermediate Similarity	NPD5898	Approved
0.7014	Intermediate Similarity	NPD6770	Approved
0.701	Intermediate Similarity	NPD5530	Phase 1
0.701	Intermediate Similarity	NPD7010	Phase 3
0.7005	Intermediate Similarity	NPD4315	Phase 2
0.7005	Intermediate Similarity	NPD7569	Approved
0.7005	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7570	Approved
0.7	Intermediate Similarity	NPD6642	Approved
0.7	Intermediate Similarity	NPD6641	Approved
0.7	Intermediate Similarity	NPD3755	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6176	Phase 1
0.6995	Remote Similarity	NPD1630	Approved
0.6995	Remote Similarity	NPD6178	Phase 3
0.6989	Remote Similarity	NPD3525	Discontinued
0.6979	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2836	Approved
0.6977	Remote Similarity	NPD8289	Discontinued
0.6964	Remote Similarity	NPD7921	Approved
0.6963	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3222	Phase 2
0.6954	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7397	Approved
0.6947	Remote Similarity	NPD7398	Approved
0.6944	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7665	Phase 2
0.6942	Remote Similarity	NPD7666	Phase 3
0.6939	Remote Similarity	NPD5016	Approved
0.6938	Remote Similarity	NPD3243	Approved
0.693	Remote Similarity	NPD3925	Approved
0.6927	Remote Similarity	NPD6452	Discontinued
0.6927	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6159	Phase 2
0.691	Remote Similarity	NPD9074	Approved
0.691	Remote Similarity	NPD9075	Approved
0.6907	Remote Similarity	NPD721	Approved
0.6905	Remote Similarity	NPD5293	Phase 2
0.6904	Remote Similarity	NPD2565	Phase 2
0.6904	Remote Similarity	NPD2564	Approved
0.6893	Remote Similarity	NPD5429	Discontinued
0.6891	Remote Similarity	NPD4204	Approved
0.6891	Remote Similarity	NPD4203	Approved
0.6884	Remote Similarity	NPD3403	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1173	Approved
0.6882	Remote Similarity	NPD5088	Discontinued
0.6875	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6716	Phase 1
0.6869	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7694	Discontinued
0.6865	Remote Similarity	NPD2511	Approved
0.6863	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2380	Approved
0.6859	Remote Similarity	NPD2381	Approved
0.6859	Remote Similarity	NPD2382	Approved
0.6853	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6962	Phase 2
0.6848	Remote Similarity	NPD212	Discontinued
0.6848	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2915	Discontinued
0.6845	Remote Similarity	NPD7001	Phase 3
0.6839	Remote Similarity	NPD2479	Phase 3
0.6839	Remote Similarity	NPD2481	Approved
0.6839	Remote Similarity	NPD1643	Phase 3
0.6837	Remote Similarity	NPD4940	Approved
0.6837	Remote Similarity	NPD6995	Phase 1
0.6837	Remote Similarity	NPD5809	Phase 3
0.6834	Remote Similarity	NPD1896	Approved
0.6828	Remote Similarity	NPD7996	Phase 2
0.6827	Remote Similarity	NPD6529	Discontinued
0.6825	Remote Similarity	NPD4897	Phase 2
0.6824	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1096	Discontinued
0.6821	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4499	Approved
0.6806	Remote Similarity	NPD6753	Phase 1
0.6806	Remote Similarity	NPD6752	Phase 1
0.6806	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD4051	Discontinued
0.6791	Remote Similarity	NPD5138	Approved
0.6791	Remote Similarity	NPD5140	Approved
0.6791	Remote Similarity	NPD5507	Approved
0.6791	Remote Similarity	NPD5506	Approved
0.6788	Remote Similarity	NPD1587	Approved
0.6784	Remote Similarity	NPD5807	Phase 2
0.6782	Remote Similarity	NPD6206	Phase 1
0.6776	Remote Similarity	NPD3258	Approved
0.6769	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4602	Approved
0.6765	Remote Similarity	NPD6479	Discontinued
0.6765	Remote Similarity	NPD4600	Approved
0.6765	Remote Similarity	NPD4601	Approved
0.6763	Remote Similarity	NPD6245	Phase 2
0.6763	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2896	Discontinued
0.676	Remote Similarity	NPD3813	Approved
0.6758	Remote Similarity	NPD1230	Approved
0.6757	Remote Similarity	NPD820	Phase 3

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