NPASS Compound

Structure

NPC129603 OpenBabel07101719152D 21 24 0 0 1 0 0 0 0 0999 V2000 1.1892 4.0762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1646 0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 1.8271 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 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4575 1.8714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4179 2.6272 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 0.0997 3.0940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 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 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8554 3.1336 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 0.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 12 19 1 6 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 17 1 6 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 21 1 0 0 0 0 17 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	289.17
Volume:	297.82
LogP:	1.651
LogD:	1.221
LogS:	-1.558
# Rotatable Bonds:	1
TPSA:	41.93
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.859
Synthetic Accessibility Score:	4.185
Fsp3:	0.647
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:	-4.727
MDCK Permeability:	1.3763959941570647e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.995
Plasma Protein Binding (PPB):	20.99013900756836%
Volume Distribution (VD):	2.945
Pgp-substrate:	75.33482360839844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.214
CYP1A2-substrate:	0.694
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.293
CYP2D6-inhibitor:	0.851
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.838

ADMET: Excretion

Clearance (CL):	10.389
Half-life (T1/2):	0.446

ADMET: Toxicity

hERG Blockers:	0.657
Human Hepatotoxicity (H-HT):	0.435
Drug-inuced Liver Injury (DILI):	0.202
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.877
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.921
Carcinogencity:	0.705
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC129603

Natural Product ID:	NPC129603
*Common Name:**	Lycoramine
IUPAC Name:	n.a.
Synonyms:	Lycoramine
Standard InCHIKey:	GJRMHIXYLGOZSE-RVSPLBMKSA-N
Standard InCHI:	InChI=1S/C17H23NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-4,12,14,19H,5-10H2,1-2H3/t12-,14-,17+/m0/s1
SMILES:	CN1CC[C@]23CC[C@@H](C[C@@H]2Oc2c(ccc(C1)c32)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2146605
PubChem CID:	12312560
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004128] Galanthamine-type amaryllidaceae 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
NPO33437	amaryllidaceae	Family	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22921081]

☑ 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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1160	Cell Line	BJ	Homo sapiens	IC50	>	50000.0	nM	PMID[531275]
NPT2468	Cell Line	G-361	Homo sapiens	IC50	>	50000.0	nM	PMID[531275]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[531275]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[531275]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[531275]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	>	50000.0	nM	PMID[531275]

☑ 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 NPC129603 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	260
0.1-0.2	1292
0.2-0.3	4162
0.3-0.4	12428
0.4-0.5	5877
0.5-0.6	10881
0.6-0.7	6358
0.7-0.8	1277
0.8-0.85	135
0.85-0.9	12
0.9-0.95	6
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9732	High Similarity	NPC65490
0.9732	High Similarity	NPC40389
0.9732	High Similarity	NPC148014
0.9732	High Similarity	NPC315707
0.9732	High Similarity	NPC78359
0.9474	High Similarity	NPC18402
0.9351	High Similarity	NPC293871
0.9351	High Similarity	NPC124433
0.8696	High Similarity	NPC284842
0.8544	High Similarity	NPC323443
0.8544	High Similarity	NPC180756
0.8528	High Similarity	NPC83198
0.8528	High Similarity	NPC204908
0.8519	High Similarity	NPC124657
0.8373	Intermediate Similarity	NPC232386
0.8373	Intermediate Similarity	NPC190783
0.8373	Intermediate Similarity	NPC152680
0.8313	Intermediate Similarity	NPC147091
0.8293	Intermediate Similarity	NPC476002
0.8284	Intermediate Similarity	NPC244554
0.8269	Intermediate Similarity	NPC476151
0.8228	Intermediate Similarity	NPC274026
0.8225	Intermediate Similarity	NPC15919
0.821	Intermediate Similarity	NPC92191
0.821	Intermediate Similarity	NPC59028
0.8205	Intermediate Similarity	NPC473934
0.8193	Intermediate Similarity	NPC290759
0.8193	Intermediate Similarity	NPC266176
0.8193	Intermediate Similarity	NPC82533
0.8193	Intermediate Similarity	NPC158148
0.8187	Intermediate Similarity	NPC475557
0.8165	Intermediate Similarity	NPC103379
0.8165	Intermediate Similarity	NPC477565
0.816	Intermediate Similarity	NPC249274
0.8155	Intermediate Similarity	NPC2314
0.8144	Intermediate Similarity	NPC75958
0.8144	Intermediate Similarity	NPC311991
0.8141	Intermediate Similarity	NPC185838
0.8133	Intermediate Similarity	NPC150879
0.8107	Intermediate Similarity	NPC49353
0.8107	Intermediate Similarity	NPC187678
0.8101	Intermediate Similarity	NPC37144
0.8101	Intermediate Similarity	NPC59907
0.8095	Intermediate Similarity	NPC470739
0.8095	Intermediate Similarity	NPC225597
0.8095	Intermediate Similarity	NPC65403
0.8095	Intermediate Similarity	NPC477640
0.8092	Intermediate Similarity	NPC9867
0.8084	Intermediate Similarity	NPC58766
0.8084	Intermediate Similarity	NPC475686
0.8072	Intermediate Similarity	NPC13916
0.8072	Intermediate Similarity	NPC264850
0.8059	Intermediate Similarity	NPC474470
0.8054	Intermediate Similarity	NPC160193
0.8052	Intermediate Similarity	NPC314682
0.8049	Intermediate Similarity	NPC97072
0.8049	Intermediate Similarity	NPC205167
0.8049	Intermediate Similarity	NPC215829
0.8041	Intermediate Similarity	NPC172403
0.8038	Intermediate Similarity	NPC179825
0.8038	Intermediate Similarity	NPC191376
0.8038	Intermediate Similarity	NPC321505
0.8036	Intermediate Similarity	NPC474475
0.8025	Intermediate Similarity	NPC130926
0.8012	Intermediate Similarity	NPC133011
0.8012	Intermediate Similarity	NPC118633
0.8012	Intermediate Similarity	NPC24465
0.8012	Intermediate Similarity	NPC148693
0.8012	Intermediate Similarity	NPC82285
0.8012	Intermediate Similarity	NPC294790
0.8	Intermediate Similarity	NPC213206
0.8	Intermediate Similarity	NPC60186
0.8	Intermediate Similarity	NPC328750
0.8	Intermediate Similarity	NPC474915
0.8	Intermediate Similarity	NPC188163
0.7987	Intermediate Similarity	NPC135538
0.7987	Intermediate Similarity	NPC428
0.7987	Intermediate Similarity	NPC24233
0.7987	Intermediate Similarity	NPC246587
0.7987	Intermediate Similarity	NPC476571
0.7987	Intermediate Similarity	NPC147390
0.7974	Intermediate Similarity	NPC131204
0.7974	Intermediate Similarity	NPC301050
0.7965	Intermediate Similarity	NPC126284
0.7955	Intermediate Similarity	NPC206900
0.7952	Intermediate Similarity	NPC320104
0.7952	Intermediate Similarity	NPC233650
0.7925	Intermediate Similarity	NPC210437
0.7925	Intermediate Similarity	NPC106295
0.7925	Intermediate Similarity	NPC51957
0.7925	Intermediate Similarity	NPC16107
0.7925	Intermediate Similarity	NPC476144
0.7919	Intermediate Similarity	NPC286119
0.7919	Intermediate Similarity	NPC305847
0.7917	Intermediate Similarity	NPC100566
0.7914	Intermediate Similarity	NPC184026
0.7914	Intermediate Similarity	NPC2413
0.7914	Intermediate Similarity	NPC193949
0.7914	Intermediate Similarity	NPC127674
0.7914	Intermediate Similarity	NPC204828
0.7914	Intermediate Similarity	NPC189266
0.7914	Intermediate Similarity	NPC54379
0.7914	Intermediate Similarity	NPC207757
0.7914	Intermediate Similarity	NPC249797
0.7914	Intermediate Similarity	NPC39701
0.7914	Intermediate Similarity	NPC244112
0.7914	Intermediate Similarity	NPC469817
0.7914	Intermediate Similarity	NPC172765
0.7914	Intermediate Similarity	NPC276588
0.7914	Intermediate Similarity	NPC78733
0.7914	Intermediate Similarity	NPC110416
0.7914	Intermediate Similarity	NPC278799
0.7914	Intermediate Similarity	NPC295691
0.7914	Intermediate Similarity	NPC5238
0.7904	Intermediate Similarity	NPC134858
0.7882	Intermediate Similarity	NPC198498
0.7882	Intermediate Similarity	NPC10908
0.7882	Intermediate Similarity	NPC276890
0.7882	Intermediate Similarity	NPC227060
0.7882	Intermediate Similarity	NPC76682
0.7882	Intermediate Similarity	NPC317145
0.7882	Intermediate Similarity	NPC63646
0.7882	Intermediate Similarity	NPC115284
0.7882	Intermediate Similarity	NPC317439
0.7875	Intermediate Similarity	NPC475959
0.7875	Intermediate Similarity	NPC7467
0.7874	Intermediate Similarity	NPC185639
0.7874	Intermediate Similarity	NPC311973
0.7874	Intermediate Similarity	NPC42663
0.7874	Intermediate Similarity	NPC30779
0.7874	Intermediate Similarity	NPC104196
0.7874	Intermediate Similarity	NPC302449
0.7874	Intermediate Similarity	NPC222661
0.7874	Intermediate Similarity	NPC290005
0.7874	Intermediate Similarity	NPC7715
0.7874	Intermediate Similarity	NPC15414
0.7874	Intermediate Similarity	NPC49075
0.7874	Intermediate Similarity	NPC285931
0.7874	Intermediate Similarity	NPC328155
0.7874	Intermediate Similarity	NPC223690
0.7874	Intermediate Similarity	NPC90998
0.7874	Intermediate Similarity	NPC181796
0.7874	Intermediate Similarity	NPC229373
0.7874	Intermediate Similarity	NPC271013
0.7874	Intermediate Similarity	NPC258657
0.7874	Intermediate Similarity	NPC54654
0.7874	Intermediate Similarity	NPC290582
0.7874	Intermediate Similarity	NPC248642
0.7874	Intermediate Similarity	NPC251735
0.7874	Intermediate Similarity	NPC279228
0.7874	Intermediate Similarity	NPC8836
0.7874	Intermediate Similarity	NPC239824
0.7874	Intermediate Similarity	NPC217748
0.7874	Intermediate Similarity	NPC182052
0.7857	Intermediate Similarity	NPC7018
0.7853	Intermediate Similarity	NPC477564
0.7853	Intermediate Similarity	NPC2295
0.7849	Intermediate Similarity	NPC241704
0.7844	Intermediate Similarity	NPC218614
0.7841	Intermediate Similarity	NPC214116
0.7836	Intermediate Similarity	NPC129518
0.7836	Intermediate Similarity	NPC41376
0.7836	Intermediate Similarity	NPC251580
0.7836	Intermediate Similarity	NPC12424
0.7831	Intermediate Similarity	NPC4304
0.7829	Intermediate Similarity	NPC274716
0.7829	Intermediate Similarity	NPC167116
0.7829	Intermediate Similarity	NPC254441
0.7829	Intermediate Similarity	NPC156576
0.7826	Intermediate Similarity	NPC207824
0.7826	Intermediate Similarity	NPC60538
0.7824	Intermediate Similarity	NPC168753
0.7824	Intermediate Similarity	NPC329911
0.7824	Intermediate Similarity	NPC118274
0.7818	Intermediate Similarity	NPC476572
0.7811	Intermediate Similarity	NPC210140
0.7811	Intermediate Similarity	NPC190332
0.7811	Intermediate Similarity	NPC252960
0.7811	Intermediate Similarity	NPC474931
0.7811	Intermediate Similarity	NPC306555
0.7811	Intermediate Similarity	NPC12053
0.7811	Intermediate Similarity	NPC145832
0.7811	Intermediate Similarity	NPC181653
0.7811	Intermediate Similarity	NPC81218
0.7811	Intermediate Similarity	NPC158376
0.7811	Intermediate Similarity	NPC117188
0.7811	Intermediate Similarity	NPC205421
0.7805	Intermediate Similarity	NPC325871
0.7805	Intermediate Similarity	NPC41178
0.7805	Intermediate Similarity	NPC138487
0.7805	Intermediate Similarity	NPC99659
0.7805	Intermediate Similarity	NPC216459
0.7798	Intermediate Similarity	NPC306843
0.7798	Intermediate Similarity	NPC169743
0.7798	Intermediate Similarity	NPC196447
0.7798	Intermediate Similarity	NPC96603
0.7798	Intermediate Similarity	NPC247972
0.7798	Intermediate Similarity	NPC136508
0.7798	Intermediate Similarity	NPC78222
0.7798	Intermediate Similarity	NPC212794

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 NPC129603 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	690
0.2-0.3	947
0.3-0.4	2274
0.4-0.5	2481
0.5-0.6	1608
0.6-0.7	736
0.7-0.8	208
0.8-0.85	21
0.85-0.9	5
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9732	High Similarity	NPD2563	Approved
0.9732	High Similarity	NPD2560	Approved
0.9355	High Similarity	NPD6071	Discontinued
0.8519	High Similarity	NPD3051	Approved
0.8466	Intermediate Similarity	NPD2970	Approved
0.8466	Intermediate Similarity	NPD2969	Approved
0.8303	Intermediate Similarity	NPD27	Approved
0.8303	Intermediate Similarity	NPD2489	Approved
0.8272	Intermediate Similarity	NPD7833	Phase 2
0.8272	Intermediate Similarity	NPD7831	Phase 2
0.8272	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD4772	Phase 2
0.8187	Intermediate Similarity	NPD4773	Phase 2
0.8046	Intermediate Similarity	NPD7906	Approved
0.8023	Intermediate Similarity	NPD4578	Approved
0.8023	Intermediate Similarity	NPD4577	Approved
0.8	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD4663	Approved
0.7987	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD4481	Phase 3
0.7949	Intermediate Similarity	NPD4236	Phase 3
0.7949	Intermediate Similarity	NPD4237	Approved
0.7941	Intermediate Similarity	NPD8156	Discontinued
0.7925	Intermediate Similarity	NPD4584	Approved
0.7922	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7313	Approved
0.7919	Intermediate Similarity	NPD7312	Approved
0.7919	Intermediate Similarity	NPD7311	Approved
0.7919	Intermediate Similarity	NPD7310	Approved
0.7895	Intermediate Similarity	NPD2238	Phase 2
0.7882	Intermediate Similarity	NPD8252	Approved
0.7882	Intermediate Similarity	NPD8099	Discontinued
0.7882	Intermediate Similarity	NPD8251	Approved
0.7874	Intermediate Similarity	NPD8054	Approved
0.7874	Intermediate Similarity	NPD8053	Approved
0.7874	Intermediate Similarity	NPD7309	Approved
0.7866	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5241	Discontinued
0.7826	Intermediate Similarity	NPD6031	Approved
0.7826	Intermediate Similarity	NPD6030	Approved
0.7826	Intermediate Similarity	NPD5976	Discontinued
0.7799	Intermediate Similarity	NPD7124	Phase 2
0.773	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5177	Phase 3
0.7722	Intermediate Similarity	NPD4162	Approved
0.7722	Intermediate Similarity	NPD3060	Approved
0.7702	Intermediate Similarity	NPD4123	Phase 3
0.7702	Intermediate Similarity	NPD1424	Approved
0.7683	Intermediate Similarity	NPD4675	Approved
0.7683	Intermediate Similarity	NPD4678	Approved
0.7669	Intermediate Similarity	NPD4210	Discontinued
0.7665	Intermediate Similarity	NPD6788	Approved
0.7665	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD2898	Approved
0.7651	Intermediate Similarity	NPD5772	Approved
0.7651	Intermediate Similarity	NPD5773	Approved
0.7643	Intermediate Similarity	NPD2161	Phase 2
0.7637	Intermediate Similarity	NPD2975	Approved
0.7637	Intermediate Similarity	NPD2973	Approved
0.7637	Intermediate Similarity	NPD2974	Approved
0.7628	Intermediate Similarity	NPD6896	Approved
0.7628	Intermediate Similarity	NPD6895	Approved
0.7625	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2677	Approved
0.7619	Intermediate Similarity	NPD4055	Discovery
0.7614	Intermediate Similarity	NPD2968	Approved
0.7614	Intermediate Similarity	NPD2971	Approved
0.7593	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6331	Phase 2
0.7561	Intermediate Similarity	NPD3687	Approved
0.7561	Intermediate Similarity	NPD3686	Approved
0.7556	Intermediate Similarity	NPD2488	Approved
0.7556	Intermediate Similarity	NPD2490	Approved
0.7529	Intermediate Similarity	NPD3365	Discontinued
0.7516	Intermediate Similarity	NPD6111	Discontinued
0.7515	Intermediate Similarity	NPD4017	Approved
0.7514	Intermediate Similarity	NPD4580	Approved
0.7485	Intermediate Similarity	NPD5720	Discontinued
0.7485	Intermediate Similarity	NPD7020	Approved
0.7485	Intermediate Similarity	NPD7019	Approved
0.7484	Intermediate Similarity	NPD4474	Approved
0.7484	Intermediate Similarity	NPD4475	Approved
0.7484	Intermediate Similarity	NPD1375	Discontinued
0.7473	Intermediate Similarity	NPD2494	Approved
0.7473	Intermediate Similarity	NPD3452	Approved
0.7473	Intermediate Similarity	NPD3450	Approved
0.7473	Intermediate Similarity	NPD2493	Approved
0.7469	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6666	Approved
0.7469	Intermediate Similarity	NPD6667	Approved
0.7439	Intermediate Similarity	NPD6090	Discontinued
0.7439	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7153	Discontinued
0.7432	Intermediate Similarity	NPD3443	Approved
0.7432	Intermediate Similarity	NPD3444	Approved
0.7432	Intermediate Similarity	NPD3445	Approved
0.7427	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6072	Discontinued
0.7419	Intermediate Similarity	NPD5718	Phase 2
0.741	Intermediate Similarity	NPD4005	Discontinued
0.7394	Intermediate Similarity	NPD3641	Approved
0.7394	Intermediate Similarity	NPD3640	Phase 3
0.7394	Intermediate Similarity	NPD3639	Approved
0.7391	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2674	Phase 3
0.7354	Intermediate Similarity	NPD4582	Approved
0.7354	Intermediate Similarity	NPD4583	Approved
0.7346	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2978	Approved
0.7337	Intermediate Similarity	NPD2977	Approved
0.7326	Intermediate Similarity	NPD5677	Discontinued
0.7302	Intermediate Similarity	NPD4002	Approved
0.7302	Intermediate Similarity	NPD4004	Approved
0.7301	Intermediate Similarity	NPD5160	Discontinued
0.7301	Intermediate Similarity	NPD3692	Discontinued
0.7289	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7298	Approved
0.7268	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5709	Phase 3
0.7267	Intermediate Similarity	NPD2668	Approved
0.7267	Intermediate Similarity	NPD2667	Approved
0.7267	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2156	Approved
0.725	Intermediate Similarity	NPD2154	Approved
0.725	Intermediate Similarity	NPD2155	Approved
0.7241	Intermediate Similarity	NPD4010	Discontinued
0.7239	Intermediate Similarity	NPD6748	Discontinued
0.7239	Intermediate Similarity	NPD7466	Approved
0.7237	Intermediate Similarity	NPD2233	Approved
0.7237	Intermediate Similarity	NPD2230	Approved
0.7237	Intermediate Similarity	NPD2232	Approved
0.7233	Intermediate Similarity	NPD2157	Approved
0.7229	Intermediate Similarity	NPD7526	Approved
0.7229	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD52	Approved
0.7229	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7296	Approved
0.7226	Intermediate Similarity	NPD1712	Approved
0.7225	Intermediate Similarity	NPD4666	Phase 3
0.7222	Intermediate Similarity	NPD2170	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7037	Approved
0.7219	Intermediate Similarity	NPD4420	Approved
0.7212	Intermediate Similarity	NPD7212	Phase 2
0.7212	Intermediate Similarity	NPD7213	Phase 3
0.7209	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4477	Approved
0.7205	Intermediate Similarity	NPD4476	Approved
0.7202	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6687	Approved
0.72	Intermediate Similarity	NPD6688	Approved
0.7197	Intermediate Similarity	NPD3145	Approved
0.7197	Intermediate Similarity	NPD3144	Approved
0.7188	Intermediate Similarity	NPD2200	Suspended
0.7184	Intermediate Similarity	NPD6107	Approved
0.7174	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7447	Phase 1
0.7169	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7549	Discontinued
0.7161	Intermediate Similarity	NPD7905	Discontinued
0.716	Intermediate Similarity	NPD6875	Approved
0.716	Intermediate Similarity	NPD6876	Approved
0.7158	Intermediate Similarity	NPD3398	Discontinued
0.7158	Intermediate Similarity	NPD3057	Approved
0.7158	Intermediate Similarity	NPD5005	Approved
0.7158	Intermediate Similarity	NPD5006	Approved
0.7135	Intermediate Similarity	NPD4585	Approved
0.7135	Intermediate Similarity	NPD4873	Discontinued
0.7134	Intermediate Similarity	NPD3027	Phase 3
0.7126	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3054	Approved
0.7125	Intermediate Similarity	NPD3052	Approved
0.7118	Intermediate Similarity	NPD7110	Phase 1
0.7118	Intermediate Similarity	NPD5089	Approved
0.7118	Intermediate Similarity	NPD5090	Approved
0.7118	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5604	Discontinued
0.7108	Intermediate Similarity	NPD1774	Approved
0.7107	Intermediate Similarity	NPD1613	Approved
0.7107	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3294	Phase 2
0.7093	Intermediate Similarity	NPD5977	Approved
0.7093	Intermediate Similarity	NPD5978	Approved
0.709	Intermediate Similarity	NPD8095	Phase 1
0.7089	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7802	Discontinued
0.7086	Intermediate Similarity	NPD2595	Approved
0.7086	Intermediate Similarity	NPD2594	Approved
0.7083	Intermediate Similarity	NPD2122	Discontinued
0.7083	Intermediate Similarity	NPD7427	Discontinued
0.7071	Intermediate Similarity	NPD7047	Phase 3
0.7068	Intermediate Similarity	NPD2972	Approved
0.7068	Intermediate Similarity	NPD3533	Approved
0.7066	Intermediate Similarity	NPD2874	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