NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	324.18
Volume:	338.086
LogP:	3.86
LogD:	3.844
LogS:	-4.713
# Rotatable Bonds:	2
TPSA:	45.33
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.918
Synthetic Accessibility Score:	5.205
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.978
MDCK Permeability:	1.6185744243557565e-05
Pgp-inhibitor:	0.095
Pgp-substrate:	0.695
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978
Plasma Protein Binding (PPB):	84.39222717285156%
Volume Distribution (VD):	2.076
Pgp-substrate:	10.637593269348145%

ADMET: Metabolism

CYP1A2-inhibitor:	0.936
CYP1A2-substrate:	0.92
CYP2C19-inhibitor:	0.851
CYP2C19-substrate:	0.818
CYP2C9-inhibitor:	0.801
CYP2C9-substrate:	0.593
CYP2D6-inhibitor:	0.889
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.698
CYP3A4-substrate:	0.639

ADMET: Excretion

Clearance (CL):	9.954
Half-life (T1/2):	0.315

ADMET: Toxicity

hERG Blockers:	0.383
Human Hepatotoxicity (H-HT):	0.413
Drug-inuced Liver Injury (DILI):	0.838
AMES Toxicity:	0.715
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.097
Carcinogencity:	0.942
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC478078

Natural Product ID:	NPC478078
*Common Name:**	(1R,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraen-11-one
IUPAC Name:	(1R,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraen-11-one
Synonyms:
Standard InCHIKey:	KQABPFRLIMUVDP-CFOBNSSQSA-N
Standard InCHI:	InChI=1S/C20H24N2O2/c1-3-12-6-11-7-15-19-18(17(23)10-22(9-11)20(12)15)14-8-13(24-2)4-5-16(14)21-19/h4-5,8,11-12,15,20-21H,3,6-7,9-10H2,1-2H3/t11-,12-,15-,20-/m0/s1
SMILES:	CC[C@H]1C[C@H]2C[C@@H]3[C@H]1N(C2)CC(=O)C4=C3NC5=C4C=C(C=C5)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122179182
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002748] Ibogan-type alkaloids

*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
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18778099]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[24773071]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	stem-bark	Pahang, Malaysia	2003-JUN	PMID[25919190]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26918761]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27077800]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29319316]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30869890]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32356659]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9376	Tabernaemontana corymbosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25	ug/ml	PMID[25919190]

☑ 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 NPC478078 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	523
0.1-0.2	2540
0.2-0.3	12294
0.3-0.4	6892
0.4-0.5	14881
0.5-0.6	2942
0.6-0.7	2068
0.7-0.8	516
0.8-0.85	25
0.85-0.9	12
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9158	High Similarity	NPC471304
0.8942	High Similarity	NPC96321
0.892	High Similarity	NPC311906
0.8806	High Similarity	NPC329793
0.8624	High Similarity	NPC474192
0.8624	High Similarity	NPC475720
0.8498	Intermediate Similarity	NPC473041
0.8478	Intermediate Similarity	NPC478083
0.8475	Intermediate Similarity	NPC475816
0.8419	Intermediate Similarity	NPC472099
0.8404	Intermediate Similarity	NPC469928
0.8356	Intermediate Similarity	NPC157931
0.8333	Intermediate Similarity	NPC473105
0.8325	Intermediate Similarity	NPC300156
0.8325	Intermediate Similarity	NPC45190
0.8274	Intermediate Similarity	NPC477066
0.8238	Intermediate Similarity	NPC477067
0.8238	Intermediate Similarity	NPC478081
0.8238	Intermediate Similarity	NPC478082
0.8233	Intermediate Similarity	NPC152768
0.8233	Intermediate Similarity	NPC148183
0.8194	Intermediate Similarity	NPC305984
0.8178	Intermediate Similarity	NPC472098
0.8174	Intermediate Similarity	NPC17437
0.8173	Intermediate Similarity	NPC329747
0.816	Intermediate Similarity	NPC475910
0.814	Intermediate Similarity	NPC478074
0.81	Intermediate Similarity	NPC21638
0.8082	Intermediate Similarity	NPC323969
0.8079	Intermediate Similarity	NPC473540
0.8045	Intermediate Similarity	NPC280799
0.8037	Intermediate Similarity	NPC288987
0.8028	Intermediate Similarity	NPC321428
0.8	Intermediate Similarity	NPC329982
0.7982	Intermediate Similarity	NPC330009
0.7973	Intermediate Similarity	NPC122436
0.7944	Intermediate Similarity	NPC270918
0.7944	Intermediate Similarity	NPC53344
0.7931	Intermediate Similarity	NPC81939
0.7926	Intermediate Similarity	NPC264176
0.7911	Intermediate Similarity	NPC471762
0.7911	Intermediate Similarity	NPC66777
0.7911	Intermediate Similarity	NPC194740
0.7909	Intermediate Similarity	NPC46561
0.7897	Intermediate Similarity	NPC475666
0.7895	Intermediate Similarity	NPC39370
0.789	Intermediate Similarity	NPC478080
0.7885	Intermediate Similarity	NPC473186
0.7882	Intermediate Similarity	NPC176127
0.787	Intermediate Similarity	NPC101350
0.7867	Intermediate Similarity	NPC257851
0.786	Intermediate Similarity	NPC4687
0.786	Intermediate Similarity	NPC249583
0.786	Intermediate Similarity	NPC477549
0.7857	Intermediate Similarity	NPC53534
0.7851	Intermediate Similarity	NPC329631
0.7826	Intermediate Similarity	NPC235685
0.7808	Intermediate Similarity	NPC39500
0.7804	Intermediate Similarity	NPC476098
0.7798	Intermediate Similarity	NPC187501
0.7793	Intermediate Similarity	NPC74360
0.7778	Intermediate Similarity	NPC478075
0.7763	Intermediate Similarity	NPC474688
0.7763	Intermediate Similarity	NPC219087
0.7759	Intermediate Similarity	NPC191489
0.7758	Intermediate Similarity	NPC276657
0.7741	Intermediate Similarity	NPC303374
0.774	Intermediate Similarity	NPC472112
0.774	Intermediate Similarity	NPC329858
0.7729	Intermediate Similarity	NPC207686
0.7717	Intermediate Similarity	NPC87413
0.7714	Intermediate Similarity	NPC81802
0.7714	Intermediate Similarity	NPC247735
0.7714	Intermediate Similarity	NPC472210
0.7714	Intermediate Similarity	NPC269886
0.7714	Intermediate Similarity	NPC472295
0.7703	Intermediate Similarity	NPC92111
0.7692	Intermediate Similarity	NPC196251
0.7692	Intermediate Similarity	NPC102338
0.7692	Intermediate Similarity	NPC111602
0.7692	Intermediate Similarity	NPC63199
0.7689	Intermediate Similarity	NPC144452
0.7686	Intermediate Similarity	NPC260434
0.7682	Intermediate Similarity	NPC310211
0.7682	Intermediate Similarity	NPC308137
0.7679	Intermediate Similarity	NPC225279
0.7672	Intermediate Similarity	NPC184680
0.7668	Intermediate Similarity	NPC303658
0.7668	Intermediate Similarity	NPC184408
0.7667	Intermediate Similarity	NPC472113
0.7664	Intermediate Similarity	NPC152620
0.7664	Intermediate Similarity	NPC249040
0.7661	Intermediate Similarity	NPC171787
0.766	Intermediate Similarity	NPC142385
0.7656	Intermediate Similarity	NPC76748
0.7656	Intermediate Similarity	NPC314333
0.7655	Intermediate Similarity	NPC322482
0.7652	Intermediate Similarity	NPC49547
0.765	Intermediate Similarity	NPC148889
0.7644	Intermediate Similarity	NPC198503
0.7639	Intermediate Similarity	NPC470785
0.7639	Intermediate Similarity	NPC470784
0.7636	Intermediate Similarity	NPC208284
0.7636	Intermediate Similarity	NPC9894
0.7634	Intermediate Similarity	NPC208084
0.7633	Intermediate Similarity	NPC315634
0.7633	Intermediate Similarity	NPC88923
0.7633	Intermediate Similarity	NPC100734
0.7632	Intermediate Similarity	NPC74575
0.763	Intermediate Similarity	NPC307963
0.7623	Intermediate Similarity	NPC169402
0.7613	Intermediate Similarity	NPC116238
0.7611	Intermediate Similarity	NPC280272
0.7608	Intermediate Similarity	NPC296527
0.7605	Intermediate Similarity	NPC63971
0.7605	Intermediate Similarity	NPC91868
0.7604	Intermediate Similarity	NPC132539
0.76	Intermediate Similarity	NPC150239
0.7588	Intermediate Similarity	NPC470018
0.7581	Intermediate Similarity	NPC254240
0.7581	Intermediate Similarity	NPC128265
0.7581	Intermediate Similarity	NPC176538
0.7581	Intermediate Similarity	NPC312870
0.7581	Intermediate Similarity	NPC199851
0.7581	Intermediate Similarity	NPC294909
0.7569	Intermediate Similarity	NPC472111
0.7558	Intermediate Similarity	NPC223427
0.7542	Intermediate Similarity	NPC72905
0.7534	Intermediate Similarity	NPC193238
0.7533	Intermediate Similarity	NPC216612
0.7522	Intermediate Similarity	NPC274640
0.7521	Intermediate Similarity	NPC15801
0.7521	Intermediate Similarity	NPC6786
0.7512	Intermediate Similarity	NPC131017
0.7512	Intermediate Similarity	NPC160381
0.7512	Intermediate Similarity	NPC276517
0.7512	Intermediate Similarity	NPC162730
0.7511	Intermediate Similarity	NPC247803
0.7511	Intermediate Similarity	NPC470020
0.75	Intermediate Similarity	NPC475844
0.75	Intermediate Similarity	NPC322064
0.75	Intermediate Similarity	NPC39679
0.7489	Intermediate Similarity	NPC471080
0.7489	Intermediate Similarity	NPC236668
0.7489	Intermediate Similarity	NPC60621
0.7489	Intermediate Similarity	NPC469592
0.7479	Intermediate Similarity	NPC473187
0.7477	Intermediate Similarity	NPC251090
0.7477	Intermediate Similarity	NPC220337
0.7477	Intermediate Similarity	NPC162484
0.7477	Intermediate Similarity	NPC472116
0.7467	Intermediate Similarity	NPC179287
0.7466	Intermediate Similarity	NPC476116
0.7455	Intermediate Similarity	NPC146976
0.7455	Intermediate Similarity	NPC118228
0.7445	Intermediate Similarity	NPC174760
0.7444	Intermediate Similarity	NPC94157
0.7431	Intermediate Similarity	NPC295898
0.7431	Intermediate Similarity	NPC474116
0.743	Intermediate Similarity	NPC19692
0.743	Intermediate Similarity	NPC220151
0.7429	Intermediate Similarity	NPC284685
0.7419	Intermediate Similarity	NPC213308
0.7418	Intermediate Similarity	NPC55493
0.7418	Intermediate Similarity	NPC472292
0.7416	Intermediate Similarity	NPC84478
0.7407	Intermediate Similarity	NPC244543
0.7406	Intermediate Similarity	NPC208522
0.7399	Intermediate Similarity	NPC294375
0.7397	Intermediate Similarity	NPC134848
0.7397	Intermediate Similarity	NPC137353
0.7397	Intermediate Similarity	NPC473800
0.7395	Intermediate Similarity	NPC245916
0.7395	Intermediate Similarity	NPC472293
0.7389	Intermediate Similarity	NPC27041
0.7386	Intermediate Similarity	NPC270515
0.7382	Intermediate Similarity	NPC474701
0.738	Intermediate Similarity	NPC210434
0.7373	Intermediate Similarity	NPC280714
0.7362	Intermediate Similarity	NPC253675
0.7357	Intermediate Similarity	NPC469594
0.7354	Intermediate Similarity	NPC309845
0.7352	Intermediate Similarity	NPC471303
0.735	Intermediate Similarity	NPC196718
0.735	Intermediate Similarity	NPC102593
0.7348	Intermediate Similarity	NPC51388
0.7342	Intermediate Similarity	NPC82548
0.7342	Intermediate Similarity	NPC41679
0.7339	Intermediate Similarity	NPC315491
0.7339	Intermediate Similarity	NPC45459
0.7333	Intermediate Similarity	NPC258480
0.7333	Intermediate Similarity	NPC472291
0.733	Intermediate Similarity	NPC475841
0.733	Intermediate Similarity	NPC474145
0.7317	Intermediate Similarity	NPC258048
0.7304	Intermediate Similarity	NPC220851
0.7303	Intermediate Similarity	NPC178858
0.7301	Intermediate Similarity	NPC16066
0.7297	Intermediate Similarity	NPC193777
0.7295	Intermediate Similarity	NPC84347

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 NPC478078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	617
0.2-0.3	846
0.3-0.4	1432
0.4-0.5	2731
0.5-0.6	2209
0.6-0.7	891
0.7-0.8	137
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8663	High Similarity	NPD4118	Clinical (unspecified phase)
0.8249	Intermediate Similarity	NPD6242	Discontinued
0.8174	Intermediate Similarity	NPD8358	Approved
0.8047	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD5293	Phase 2
0.7965	Intermediate Similarity	NPD4885	Approved
0.7854	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD4558	Phase 2
0.7828	Intermediate Similarity	NPD4429	Discontinued
0.782	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD3393	Approved
0.7818	Intermediate Similarity	NPD3389	Approved
0.7818	Intermediate Similarity	NPD3394	Approved
0.7797	Intermediate Similarity	NPD4952	Phase 3
0.7768	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7708	Approved
0.7742	Intermediate Similarity	NPD5658	Approved
0.7725	Intermediate Similarity	NPD6790	Phase 1
0.7706	Intermediate Similarity	NPD3006	Discontinued
0.7696	Intermediate Similarity	NPD4373	Phase 2
0.7656	Intermediate Similarity	NPD4499	Approved
0.7633	Intermediate Similarity	NPD7803	Approved
0.763	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1038	Approved
0.7611	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD4501	Approved
0.7581	Intermediate Similarity	NPD4500	Approved
0.7565	Intermediate Similarity	NPD5479	Discontinued
0.7534	Intermediate Similarity	NPD3257	Approved
0.7531	Intermediate Similarity	NPD8091	Phase 3
0.7512	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD5632	Approved
0.75	Intermediate Similarity	NPD2509	Approved
0.75	Intermediate Similarity	NPD6376	Discontinued
0.75	Intermediate Similarity	NPD2510	Approved
0.7489	Intermediate Similarity	NPD5022	Discontinued
0.7489	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD3258	Approved
0.7478	Intermediate Similarity	NPD4845	Discontinued
0.7478	Intermediate Similarity	NPD7994	Phase 2
0.7429	Intermediate Similarity	NPD7956	Approved
0.7429	Intermediate Similarity	NPD7955	Approved
0.7427	Intermediate Similarity	NPD5482	Discontinued
0.7403	Intermediate Similarity	NPD3259	Approved
0.7399	Intermediate Similarity	NPD5416	Discontinued
0.7398	Intermediate Similarity	NPD6530	Approved
0.7398	Intermediate Similarity	NPD6531	Approved
0.7397	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4418	Discontinued
0.7339	Intermediate Similarity	NPD484	Approved
0.7336	Intermediate Similarity	NPD8463	Approved
0.7325	Intermediate Similarity	NPD6770	Approved
0.7319	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD4506	Discontinued
0.7304	Intermediate Similarity	NPD6209	Approved
0.7301	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7453	Approved
0.7297	Intermediate Similarity	NPD7452	Approved
0.7285	Intermediate Similarity	NPD3947	Discontinued
0.7253	Intermediate Similarity	NPD4328	Approved
0.7252	Intermediate Similarity	NPD3507	Phase 2
0.7243	Intermediate Similarity	NPD8102	Discontinued
0.7241	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8016	Phase 3
0.7238	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5488	Discontinued
0.7222	Intermediate Similarity	NPD5559	Phase 2
0.722	Intermediate Similarity	NPD7222	Phase 2
0.7212	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4795	Phase 2
0.7195	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD1659	Phase 1
0.7188	Intermediate Similarity	NPD2189	Approved
0.7188	Intermediate Similarity	NPD2187	Approved
0.7188	Intermediate Similarity	NPD2916	Discontinued
0.7182	Intermediate Similarity	NPD4601	Approved
0.7182	Intermediate Similarity	NPD4600	Approved
0.7175	Intermediate Similarity	NPD3003	Approved
0.7161	Intermediate Similarity	NPD6962	Phase 2
0.7155	Intermediate Similarity	NPD4368	Phase 2
0.713	Intermediate Similarity	NPD4038	Approved
0.713	Intermediate Similarity	NPD4122	Approved
0.713	Intermediate Similarity	NPD4034	Approved
0.713	Intermediate Similarity	NPD4036	Approved
0.713	Intermediate Similarity	NPD4039	Approved
0.713	Intermediate Similarity	NPD32	Approved
0.713	Intermediate Similarity	NPD4035	Approved
0.713	Intermediate Similarity	NPD4037	Approved
0.713	Intermediate Similarity	NPD5901	Discontinued
0.713	Intermediate Similarity	NPD31	Approved
0.713	Intermediate Similarity	NPD4033	Approved
0.7126	Intermediate Similarity	NPD8364	Approved
0.7126	Intermediate Similarity	NPD8363	Approved
0.7123	Intermediate Similarity	NPD5003	Discontinued
0.712	Intermediate Similarity	NPD6228	Discontinued
0.7118	Intermediate Similarity	NPD5612	Discontinued
0.7113	Intermediate Similarity	NPD7853	Phase 2
0.7109	Intermediate Similarity	NPD5473	Discontinued
0.7107	Intermediate Similarity	NPD6716	Phase 1
0.7106	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3945	Discontinued
0.7104	Intermediate Similarity	NPD1739	Approved
0.7104	Intermediate Similarity	NPD1740	Approved
0.7082	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5450	Discontinued
0.7074	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7796	Approved
0.7059	Intermediate Similarity	NPD1768	Approved
0.7059	Intermediate Similarity	NPD7797	Approved
0.7059	Intermediate Similarity	NPD3825	Phase 3
0.7056	Intermediate Similarity	NPD3354	Phase 2
0.7054	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7046	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4850	Phase 1
0.7027	Intermediate Similarity	NPD8465	Approved
0.7027	Intermediate Similarity	NPD8467	Approved
0.7027	Intermediate Similarity	NPD8466	Approved
0.702	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5186	Approved
0.7019	Intermediate Similarity	NPD5183	Approved
0.7009	Intermediate Similarity	NPD6176	Phase 1
0.7004	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2951	Discontinued
0.7	Intermediate Similarity	NPD5512	Phase 3
0.6996	Remote Similarity	NPD7417	Discontinued
0.6995	Remote Similarity	NPD4203	Approved
0.6995	Remote Similarity	NPD4204	Approved
0.6991	Remote Similarity	NPD4948	Discontinued
0.6987	Remote Similarity	NPD7455	Approved
0.6987	Remote Similarity	NPD5866	Approved
0.6987	Remote Similarity	NPD7454	Approved
0.6986	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7395	Discontinued
0.6972	Remote Similarity	NPD5913	Phase 3
0.6972	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7194	Discontinued
0.6953	Remote Similarity	NPD3402	Phase 1
0.6951	Remote Similarity	NPD8100	Phase 3
0.6947	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5601	Phase 2
0.6947	Remote Similarity	NPD5530	Phase 1
0.6944	Remote Similarity	NPD5256	Discontinued
0.6936	Remote Similarity	NPD6995	Phase 1
0.6935	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD2564	Approved
0.6927	Remote Similarity	NPD2565	Phase 2
0.6926	Remote Similarity	NPD5902	Approved
0.6926	Remote Similarity	NPD5903	Approved
0.6926	Remote Similarity	NPD4897	Phase 2
0.6923	Remote Similarity	NPD6276	Discontinued
0.6923	Remote Similarity	NPD5930	Phase 3
0.6923	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.692	Remote Similarity	NPD8459	Approved
0.692	Remote Similarity	NPD8426	Approved
0.692	Remote Similarity	NPD8425	Approved
0.692	Remote Similarity	NPD8460	Approved
0.6917	Remote Similarity	NPD7031	Phase 1
0.6916	Remote Similarity	NPD5429	Discontinued
0.691	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6568	Discontinued
0.691	Remote Similarity	NPD7878	Phase 2
0.6907	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3920	Phase 2
0.6901	Remote Similarity	NPD5891	Approved
0.6898	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8429	Approved
0.6897	Remote Similarity	NPD8428	Approved
0.6897	Remote Similarity	NPD8427	Approved
0.6895	Remote Similarity	NPD4369	Phase 2
0.6887	Remote Similarity	NPD7925	Phase 2
0.6887	Remote Similarity	NPD7924	Phase 2
0.6885	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3925	Approved
0.6875	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7688	Phase 1
0.6872	Remote Similarity	NPD8403	Phase 1
0.687	Remote Similarity	NPD4502	Phase 2
0.687	Remote Similarity	NPD7470	Discontinued
0.687	Remote Similarity	NPD5475	Discontinued
0.6867	Remote Similarity	NPD8101	Phase 3
0.6867	Remote Similarity	NPD3986	Discontinued
0.6867	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5850	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