NPASS Compound

Structure

NPC474121 OpenBabel07101718182D 26 29 0 0 1 0 0 0 0 0999 V2000 -5.2992 -0.4184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 -1.7680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 -0.5206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4904 2.0045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4532 -0.9878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7833 2.7116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2625 0.5435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2575 1.7529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3784 1.0108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5317 0.4787 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1207 -0.0372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 2 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 -4.2999 -0.4558 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1199 0.0012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8319 -1.3025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6543 -0.9218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7895 2.5996 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 17 2 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 22 1 0 0 0 0 10 26 1 0 0 0 0 11 14 1 0 0 0 0 11 18 2 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 16 20 1 1 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 19 1 6 0 0 0 22 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.17
Volume:	361.586
LogP:	1.228
LogD:	1.436
LogS:	-0.446
# Rotatable Bonds:	3
TPSA:	74.38
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.388
Synthetic Accessibility Score:	4.59
Fsp3:	0.45
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:	-5.629
MDCK Permeability:	1.4165572792990133e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.45
20% Bioavailability (F20%):	0.687
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.671
Plasma Protein Binding (PPB):	29.350723266601562%
Volume Distribution (VD):	1.906
Pgp-substrate:	75.46355438232422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.851
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.597
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.377
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.58
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.298

ADMET: Excretion

Clearance (CL):	10.358
Half-life (T1/2):	0.942

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.242
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.336
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.05
Carcinogencity:	0.966
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.839

Download Data

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

Natural Product: NPC474121

Natural Product ID:	NPC474121
*Common Name:**	Alstilobanine D
IUPAC Name:	methyl (2R,4aS,5S)-5-(1H-indol-2-yl)-2-methyl-2-oxido-1,3,4,4a,6,8-hexahydrooxepino[4,5-c]pyridin-2-ium-5-carboxylate
Synonyms:	Alstilobanine D
Standard InCHIKey:	NHKZFALDMLZGHK-XUEUYAKLSA-N
Standard InCHI:	InChI=1S/C20H24N2O4/c1-22(24)9-7-16-15(12-22)8-10-26-13-20(16,19(23)25-2)18-11-14-5-3-4-6-17(14)21-18/h3-6,8,11,16,21H,7,9-10,12-13H2,1-2H3/t16-,20-,22+/m0/s1
SMILES:	C[N+]1(CCC2C(=CCOCC2(C3=CC4=CC=CC=C4N3)C(=O)OC)C1)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462328
PubChem CID:	44561424
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524603]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Others	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	10.0	%	PMID[452702]

☑ 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 NPC474121 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	299
0.1-0.2	1452
0.2-0.3	7078
0.3-0.4	20419
0.4-0.5	8358
0.5-0.6	2437
0.6-0.7	2092
0.7-0.8	505
0.8-0.85	38
0.85-0.9	15
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9213	High Similarity	NPC55493
0.8978	High Similarity	NPC475847
0.8978	High Similarity	NPC185742
0.8811	High Similarity	NPC241024
0.8466	Intermediate Similarity	NPC214428
0.8438	Intermediate Similarity	NPC277350
0.8281	Intermediate Similarity	NPC162730
0.828	Intermediate Similarity	NPC329858
0.828	Intermediate Similarity	NPC314333
0.8187	Intermediate Similarity	NPC474116
0.7979	Intermediate Similarity	NPC52557
0.791	Intermediate Similarity	NPC475778
0.785	Intermediate Similarity	NPC469743
0.7842	Intermediate Similarity	NPC175474
0.7842	Intermediate Similarity	NPC102338
0.7842	Intermediate Similarity	NPC63199
0.7842	Intermediate Similarity	NPC111602
0.7842	Intermediate Similarity	NPC196251
0.7811	Intermediate Similarity	NPC234999
0.7692	Intermediate Similarity	NPC245916
0.768	Intermediate Similarity	NPC472295
0.768	Intermediate Similarity	NPC269886
0.768	Intermediate Similarity	NPC247735
0.768	Intermediate Similarity	NPC81802
0.768	Intermediate Similarity	NPC472210
0.7641	Intermediate Similarity	NPC220151
0.7641	Intermediate Similarity	NPC19692
0.7638	Intermediate Similarity	NPC137589
0.7633	Intermediate Similarity	NPC473041
0.7633	Intermediate Similarity	NPC96321
0.7566	Intermediate Similarity	NPC469896
0.7538	Intermediate Similarity	NPC79129
0.7538	Intermediate Similarity	NPC254240
0.7538	Intermediate Similarity	NPC312870
0.7538	Intermediate Similarity	NPC195461
0.7538	Intermediate Similarity	NPC313985
0.7538	Intermediate Similarity	NPC81654
0.7538	Intermediate Similarity	NPC294909
0.7538	Intermediate Similarity	NPC128265
0.7538	Intermediate Similarity	NPC249150
0.7538	Intermediate Similarity	NPC49196
0.7538	Intermediate Similarity	NPC199851
0.7536	Intermediate Similarity	NPC330009
0.7536	Intermediate Similarity	NPC469928
0.7449	Intermediate Similarity	NPC472113
0.7437	Intermediate Similarity	NPC50503
0.7436	Intermediate Similarity	NPC472112
0.7395	Intermediate Similarity	NPC311906
0.7387	Intermediate Similarity	NPC469736
0.7373	Intermediate Similarity	NPC475720
0.7373	Intermediate Similarity	NPC474192
0.7371	Intermediate Similarity	NPC160381
0.7368	Intermediate Similarity	NPC148183
0.7368	Intermediate Similarity	NPC152768
0.736	Intermediate Similarity	NPC472292
0.7358	Intermediate Similarity	NPC472119
0.7351	Intermediate Similarity	NPC469541
0.735	Intermediate Similarity	NPC67288
0.7339	Intermediate Similarity	NPC473105
0.7337	Intermediate Similarity	NPC472293
0.733	Intermediate Similarity	NPC219336
0.7321	Intermediate Similarity	NPC477979
0.7313	Intermediate Similarity	NPC472297
0.7313	Intermediate Similarity	NPC472296
0.7277	Intermediate Similarity	NPC15573
0.7277	Intermediate Similarity	NPC145885
0.7277	Intermediate Similarity	NPC14113
0.7277	Intermediate Similarity	NPC217372
0.7277	Intermediate Similarity	NPC84827
0.7277	Intermediate Similarity	NPC183662
0.7277	Intermediate Similarity	NPC2395
0.7273	Intermediate Similarity	NPC472291
0.724	Intermediate Similarity	NPC213468
0.7233	Intermediate Similarity	NPC477065
0.7231	Intermediate Similarity	NPC472107
0.7231	Intermediate Similarity	NPC79062
0.7225	Intermediate Similarity	NPC84347
0.7225	Intermediate Similarity	NPC118940
0.7222	Intermediate Similarity	NPC138370
0.7212	Intermediate Similarity	NPC471304
0.7212	Intermediate Similarity	NPC123839
0.7194	Intermediate Similarity	NPC235684
0.7189	Intermediate Similarity	NPC469720
0.7188	Intermediate Similarity	NPC28848
0.7188	Intermediate Similarity	NPC14325
0.7183	Intermediate Similarity	NPC52254
0.7176	Intermediate Similarity	NPC235885
0.7176	Intermediate Similarity	NPC21638
0.7175	Intermediate Similarity	NPC475816
0.717	Intermediate Similarity	NPC312645
0.7157	Intermediate Similarity	NPC472323
0.7143	Intermediate Similarity	NPC78020
0.7143	Intermediate Similarity	NPC472209
0.7136	Intermediate Similarity	NPC132539
0.7136	Intermediate Similarity	NPC82070
0.7135	Intermediate Similarity	NPC267885
0.7128	Intermediate Similarity	NPC472108
0.7128	Intermediate Similarity	NPC19679
0.7128	Intermediate Similarity	NPC139291
0.7122	Intermediate Similarity	NPC476874
0.712	Intermediate Similarity	NPC191310
0.7115	Intermediate Similarity	NPC258062
0.7115	Intermediate Similarity	NPC266249
0.7115	Intermediate Similarity	NPC127677
0.7109	Intermediate Similarity	NPC221100
0.7109	Intermediate Similarity	NPC234078
0.7109	Intermediate Similarity	NPC229348
0.7098	Intermediate Similarity	NPC234987
0.7098	Intermediate Similarity	NPC111275
0.7087	Intermediate Similarity	NPC98715
0.7083	Intermediate Similarity	NPC13367
0.7083	Intermediate Similarity	NPC149155
0.7083	Intermediate Similarity	NPC110500
0.7083	Intermediate Similarity	NPC203468
0.7081	Intermediate Similarity	NPC271862
0.7077	Intermediate Similarity	NPC71037
0.7075	Intermediate Similarity	NPC474412
0.7074	Intermediate Similarity	NPC271797
0.7074	Intermediate Similarity	NPC21174
0.7073	Intermediate Similarity	NPC300183
0.707	Intermediate Similarity	NPC472099
0.7067	Intermediate Similarity	NPC315545
0.7067	Intermediate Similarity	NPC474905
0.7067	Intermediate Similarity	NPC225821
0.7067	Intermediate Similarity	NPC46225
0.7067	Intermediate Similarity	NPC314297
0.7064	Intermediate Similarity	NPC472762
0.7062	Intermediate Similarity	NPC248041
0.7062	Intermediate Similarity	NPC283219
0.7062	Intermediate Similarity	NPC126709
0.7059	Intermediate Similarity	NPC123395
0.7056	Intermediate Similarity	NPC280290
0.7053	Intermediate Similarity	NPC317430
0.7051	Intermediate Similarity	NPC475271
0.705	Intermediate Similarity	NPC472097
0.7042	Intermediate Similarity	NPC36405
0.7042	Intermediate Similarity	NPC74969
0.7041	Intermediate Similarity	NPC143533
0.7039	Intermediate Similarity	NPC260900
0.7039	Intermediate Similarity	NPC193761
0.7031	Intermediate Similarity	NPC472123
0.703	Intermediate Similarity	NPC276517
0.7028	Intermediate Similarity	NPC89508
0.7027	Intermediate Similarity	NPC161827
0.7026	Intermediate Similarity	NPC15840
0.702	Intermediate Similarity	NPC66210
0.702	Intermediate Similarity	NPC315555
0.7019	Intermediate Similarity	NPC313796
0.7019	Intermediate Similarity	NPC315638
0.7019	Intermediate Similarity	NPC313345
0.7019	Intermediate Similarity	NPC314855
0.701	Intermediate Similarity	NPC102008
0.701	Intermediate Similarity	NPC211997
0.7005	Intermediate Similarity	NPC165599
0.7005	Intermediate Similarity	NPC258480
0.7	Intermediate Similarity	NPC478158
0.7	Intermediate Similarity	NPC33949
0.6995	Remote Similarity	NPC79356
0.6995	Remote Similarity	NPC329688
0.6995	Remote Similarity	NPC189812
0.6995	Remote Similarity	NPC11445
0.6995	Remote Similarity	NPC102592
0.6995	Remote Similarity	NPC478157
0.6989	Remote Similarity	NPC285469
0.6981	Remote Similarity	NPC472098
0.6981	Remote Similarity	NPC87856
0.6981	Remote Similarity	NPC151976
0.6979	Remote Similarity	NPC6982
0.6977	Remote Similarity	NPC281049
0.6976	Remote Similarity	NPC74413
0.6974	Remote Similarity	NPC55772
0.6974	Remote Similarity	NPC81939
0.6971	Remote Similarity	NPC314648
0.697	Remote Similarity	NPC282103
0.697	Remote Similarity	NPC473189
0.6968	Remote Similarity	NPC143457
0.6967	Remote Similarity	NPC314834
0.6963	Remote Similarity	NPC476114
0.6963	Remote Similarity	NPC132211
0.6961	Remote Similarity	NPC141454
0.696	Remote Similarity	NPC473540
0.6959	Remote Similarity	NPC134586
0.6954	Remote Similarity	NPC472104
0.6953	Remote Similarity	NPC478080
0.695	Remote Similarity	NPC32771
0.695	Remote Similarity	NPC321708
0.6948	Remote Similarity	NPC267965
0.6946	Remote Similarity	NPC157828
0.6946	Remote Similarity	NPC181502
0.6946	Remote Similarity	NPC85066
0.6946	Remote Similarity	NPC195239
0.6943	Remote Similarity	NPC34508
0.6943	Remote Similarity	NPC475666
0.6938	Remote Similarity	NPC18661
0.6937	Remote Similarity	NPC14288
0.6935	Remote Similarity	NPC311858
0.6935	Remote Similarity	NPC62749
0.693	Remote Similarity	NPC305984
0.693	Remote Similarity	NPC169402
0.6927	Remote Similarity	NPC306376

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 NPC474121 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	511
0.2-0.3	673
0.3-0.4	1418
0.4-0.5	2782
0.5-0.6	2674
0.6-0.7	824
0.7-0.8	91
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.828	Intermediate Similarity	NPD4499	Approved
0.7778	Intermediate Similarity	NPD6176	Phase 1
0.7761	Intermediate Similarity	NPD4506	Discontinued
0.7734	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD5003	Discontinued
0.7596	Intermediate Similarity	NPD6770	Approved
0.7538	Intermediate Similarity	NPD4501	Approved
0.7538	Intermediate Similarity	NPD4601	Approved
0.7538	Intermediate Similarity	NPD4500	Approved
0.7538	Intermediate Similarity	NPD4600	Approved
0.7512	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2510	Approved
0.7451	Intermediate Similarity	NPD2509	Approved
0.7436	Intermediate Similarity	NPD2565	Phase 2
0.7436	Intermediate Similarity	NPD2564	Approved
0.7419	Intermediate Similarity	NPD2844	Phase 3
0.7353	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7470	Discontinued
0.7296	Intermediate Similarity	NPD4334	Discontinued
0.7286	Intermediate Similarity	NPD3394	Approved
0.7286	Intermediate Similarity	NPD3393	Approved
0.7286	Intermediate Similarity	NPD3389	Approved
0.7216	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD2094	Phase 2
0.7128	Intermediate Similarity	NPD2092	Phase 2
0.7128	Intermediate Similarity	NPD2095	Phase 2
0.7115	Intermediate Similarity	NPD8399	Phase 1
0.7115	Intermediate Similarity	NPD8423	Phase 2
0.71	Intermediate Similarity	NPD4315	Phase 2
0.7092	Intermediate Similarity	NPD2091	Phase 2
0.7092	Intermediate Similarity	NPD2096	Phase 2
0.7087	Intermediate Similarity	NPD2920	Discontinued
0.7083	Intermediate Similarity	NPD482	Approved
0.7081	Intermediate Similarity	NPD6529	Discontinued
0.7071	Intermediate Similarity	NPD4948	Discontinued
0.7053	Intermediate Similarity	NPD56	Approved
0.7053	Intermediate Similarity	NPD8282	Approved
0.7053	Intermediate Similarity	NPD8283	Approved
0.7027	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7777	Approved
0.701	Intermediate Similarity	NPD7778	Approved
0.701	Intermediate Similarity	NPD53	Approved
0.7005	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5293	Phase 2
0.6979	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD6249	Phase 2
0.6976	Remote Similarity	NPD6248	Phase 2
0.6971	Remote Similarity	NPD5901	Discontinued
0.6971	Remote Similarity	NPD5426	Phase 3
0.6971	Remote Similarity	NPD3947	Discontinued
0.6954	Remote Similarity	NPD5596	Phase 2
0.6943	Remote Similarity	NPD750	Phase 2
0.6942	Remote Similarity	NPD6479	Discontinued
0.6935	Remote Similarity	NPD5444	Phase 1
0.6934	Remote Similarity	NPD5475	Discontinued
0.6927	Remote Similarity	NPD7946	Pre-registration
0.6923	Remote Similarity	NPD6641	Approved
0.6923	Remote Similarity	NPD6642	Approved
0.6923	Remote Similarity	NPD5487	Phase 1
0.6913	Remote Similarity	NPD8358	Approved
0.6911	Remote Similarity	NPD7864	Approved
0.6911	Remote Similarity	NPD7863	Approved
0.689	Remote Similarity	NPD8098	Approved
0.6881	Remote Similarity	NPD5913	Phase 3
0.6881	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6206	Phase 1
0.6875	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7866	Approved
0.6869	Remote Similarity	NPD3794	Approved
0.6869	Remote Similarity	NPD3795	Approved
0.686	Remote Similarity	NPD5427	Suspended
0.6857	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7010	Phase 3
0.6853	Remote Similarity	NPD5899	Approved
0.6853	Remote Similarity	NPD5898	Approved
0.6853	Remote Similarity	NPD5897	Approved
0.6852	Remote Similarity	NPD8325	Phase 3
0.6852	Remote Similarity	NPD8326	Phase 3
0.6852	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8072	Approved
0.6839	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.682	Remote Similarity	NPD7878	Phase 2
0.682	Remote Similarity	NPD5632	Approved
0.6812	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD8160	Phase 2
0.6802	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5075	Discontinued
0.6798	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5104	Approved
0.6782	Remote Similarity	NPD1534	Approved
0.678	Remote Similarity	NPD4602	Approved
0.6776	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4462	Approved
0.6774	Remote Similarity	NPD4463	Approved
0.6773	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6182	Approved
0.6769	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD43	Approved
0.6759	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1326	Approved
0.6753	Remote Similarity	NPD1325	Approved
0.6748	Remote Similarity	NPD5512	Phase 3
0.6731	Remote Similarity	NPD6999	Discontinued
0.6731	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5138	Approved
0.6719	Remote Similarity	NPD5140	Approved
0.6716	Remote Similarity	NPD6227	Discontinued
0.6702	Remote Similarity	NPD2511	Approved
0.6699	Remote Similarity	NPD4427	Phase 2
0.6699	Remote Similarity	NPD484	Approved
0.6698	Remote Similarity	NPD7001	Phase 3
0.6698	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2915	Discontinued
0.6683	Remote Similarity	NPD6261	Phase 3
0.6683	Remote Similarity	NPD4397	Phase 1
0.6682	Remote Similarity	NPD1996	Discontinued
0.6682	Remote Similarity	NPD3777	Phase 3
0.6681	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7865	Approved
0.6667	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8097	Phase 3
0.6667	Remote Similarity	NPD8096	Phase 3
0.6667	Remote Similarity	NPD6226	Phase 3
0.6667	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2144	Approved
0.6653	Remote Similarity	NPD7956	Approved
0.6653	Remote Similarity	NPD7955	Approved
0.6651	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5065	Approved
0.665	Remote Similarity	NPD3038	Discontinued
0.665	Remote Similarity	NPD3435	Discontinued
0.6649	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7688	Phase 1
0.6636	Remote Similarity	NPD7404	Approved
0.6635	Remote Similarity	NPD8073	Approved
0.6633	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7708	Approved
0.662	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7957	Phase 1
0.6615	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD4885	Approved
0.6608	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4897	Phase 2
0.6606	Remote Similarity	NPD3280	Approved
0.6606	Remote Similarity	NPD6242	Discontinued
0.66	Remote Similarity	NPD5473	Discontinued
0.66	Remote Similarity	NPD6452	Discontinued
0.6598	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4952	Phase 3
0.659	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6550	Discontinued
0.6584	Remote Similarity	NPD3436	Approved
0.6584	Remote Similarity	NPD7803	Approved
0.6583	Remote Similarity	NPD7869	Discontinued
0.6576	Remote Similarity	NPD1592	Phase 3
0.6575	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD5482	Discontinued
0.6567	Remote Similarity	NPD3178	Discontinued
0.6567	Remote Similarity	NPD4203	Approved
0.6567	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD4204	Approved
0.6566	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2213	Approved
0.6562	Remote Similarity	NPD2214	Approved
0.6561	Remote Similarity	NPD2882	Phase 1
0.6561	Remote Similarity	NPD7882	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD5658	Approved
0.6553	Remote Similarity	NPD2336	Approved
0.655	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6995	Phase 1
0.6546	Remote Similarity	NPD8466	Approved
0.6546	Remote Similarity	NPD8465	Approved
0.6546	Remote Similarity	NPD8467	Approved
0.6545	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD5416	Discontinued
0.6538	Remote Similarity	NPD4418	Discontinued
0.6538	Remote Similarity	NPD7619	Phase 3
0.6538	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7618	Phase 3
0.6537	Remote Similarity	NPD7233	Approved
0.6537	Remote Similarity	NPD7234	Approved
0.6533	Remote Similarity	NPD5471	Phase 3
0.6531	Remote Similarity	NPD5069	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data