NPASS Compound

Structure

NPC6436 OpenBabel07101718232D 21 24 0 0 1 0 0 0 0 0999 V2000 5.3373 -0.1426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3067 2.2530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7757 -0.3311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1490 1.1286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2507 0.9948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3959 0.1947 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0102 -0.0568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8650 0.7433 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 1.7796 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.4853 1.2691 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 -0.9781 -0.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 11 1 0 0 0 0 6 14 2 0 0 0 0 7 10 1 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 1 1 6 0 0 0 11 12 1 0 0 0 0 11 16 2 0 0 0 0 12 7 1 6 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 13 17 2 0 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 15 8 1 1 0 0 0 15 19 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.08
Volume:	307.884
LogP:	4.775
LogD:	4.062
LogS:	-5.366
# Rotatable Bonds:	1
TPSA:	17.4
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.785
Synthetic Accessibility Score:	3.932
Fsp3:	0.529
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.677
MDCK Permeability:	2.441757169435732e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	94.32577514648438%
Volume Distribution (VD):	3.256
Pgp-substrate:	2.2422852516174316%

ADMET: Metabolism

CYP1A2-inhibitor:	0.899
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.577
CYP2C19-substrate:	0.961
CYP2C9-inhibitor:	0.139
CYP2C9-substrate:	0.292
CYP2D6-inhibitor:	0.965
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.156
CYP3A4-substrate:	0.913

ADMET: Excretion

Clearance (CL):	4.702
Half-life (T1/2):	0.442

ADMET: Toxicity

hERG Blockers:	0.707
Human Hepatotoxicity (H-HT):	0.824
Drug-inuced Liver Injury (DILI):	0.695
AMES Toxicity:	0.506
Rat Oral Acute Toxicity:	0.714
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.71
Carcinogencity:	0.536
Eye Corrosion:	0.004
Eye Irritation:	0.026
Respiratory Toxicity:	0.904

Download Data

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

Natural Product: NPC6436

Natural Product ID:	NPC6436
*Common Name:**	Pibocin B
IUPAC Name:	(6aR,9R,10aR)-5-bromo-4-methoxy-7,9-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline
Synonyms:	pibocin B
Standard InCHIKey:	ZCNGIHGSYMIIIR-IXPVHAAZSA-N
Standard InCHI:	InChI=1S/C17H21BrN2O/c1-10-7-12-11-5-4-6-14-16(11)13(17(18)20(14)21-3)8-15(12)19(2)9-10/h4-6,10,12,15H,7-9H2,1-3H3/t10-,12-,15-/m1/s1
SMILES:	COn1c(Br)c2c3c1cccc3[C@@H]1[C@@H](C2)N(C)C[C@@H](C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491189
PubChem CID:	9975094
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002679] Ergoline and derivatives [CHEMONTID:0002747] Clavines 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
NPO33386	Eudistoma sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10346975]
NPO33386	Eudistoma sp.	Species	n.a.	n.a.	n.a.	Far-Eastern	n.a.	PMID[11754612]
NPO33386	Eudistoma sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12608864]
NPO33386	Eudistoma sp.	Species	n.a.	n.a.	n.a.	Korean	n.a.	PMID[18247569]

☑ 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
ED50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	25.0	ug ml-1	PMID[464210]

☑ 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 NPC6436 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	825
0.1-0.2	6204
0.2-0.3	21442
0.3-0.4	8077
0.4-0.5	2967
0.5-0.6	2155
0.6-0.7	873
0.7-0.8	149
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.871	High Similarity	NPC51054
0.8452	Intermediate Similarity	NPC33421
0.8137	Intermediate Similarity	NPC56765
0.7987	Intermediate Similarity	NPC104483
0.7939	Intermediate Similarity	NPC195507
0.7939	Intermediate Similarity	NPC2165
0.7914	Intermediate Similarity	NPC318065
0.7914	Intermediate Similarity	NPC206819
0.7862	Intermediate Similarity	NPC21605
0.7771	Intermediate Similarity	NPC473868
0.7771	Intermediate Similarity	NPC63157
0.7756	Intermediate Similarity	NPC316811
0.7742	Intermediate Similarity	NPC314102
0.7742	Intermediate Similarity	NPC251722
0.7722	Intermediate Similarity	NPC20144
0.7719	Intermediate Similarity	NPC121903
0.7707	Intermediate Similarity	NPC59084
0.7702	Intermediate Similarity	NPC2272
0.7701	Intermediate Similarity	NPC19679
0.7697	Intermediate Similarity	NPC41257
0.7692	Intermediate Similarity	NPC169433
0.7692	Intermediate Similarity	NPC194411
0.7679	Intermediate Similarity	NPC109447
0.7665	Intermediate Similarity	NPC90723
0.7661	Intermediate Similarity	NPC275305
0.7661	Intermediate Similarity	NPC37423
0.7651	Intermediate Similarity	NPC215584
0.7651	Intermediate Similarity	NPC44773
0.7651	Intermediate Similarity	NPC122718
0.7643	Intermediate Similarity	NPC88097
0.764	Intermediate Similarity	NPC477134
0.764	Intermediate Similarity	NPC470111
0.7636	Intermediate Similarity	NPC286427
0.763	Intermediate Similarity	NPC215795
0.763	Intermediate Similarity	NPC176199
0.7613	Intermediate Similarity	NPC198988
0.7595	Intermediate Similarity	NPC2949
0.7572	Intermediate Similarity	NPC68354
0.7564	Intermediate Similarity	NPC325252
0.7561	Intermediate Similarity	NPC200743
0.7534	Intermediate Similarity	NPC81561
0.7532	Intermediate Similarity	NPC312092
0.75	Intermediate Similarity	NPC215519
0.7483	Intermediate Similarity	NPC54102
0.7483	Intermediate Similarity	NPC162689
0.7466	Intermediate Similarity	NPC148140
0.7457	Intermediate Similarity	NPC189812
0.7457	Intermediate Similarity	NPC329688
0.7456	Intermediate Similarity	NPC247987
0.7444	Intermediate Similarity	NPC95783
0.744	Intermediate Similarity	NPC255229
0.744	Intermediate Similarity	NPC81229
0.7439	Intermediate Similarity	NPC40070
0.7419	Intermediate Similarity	NPC475450
0.7414	Intermediate Similarity	NPC474958
0.741	Intermediate Similarity	NPC34844
0.7407	Intermediate Similarity	NPC470440
0.7407	Intermediate Similarity	NPC285731
0.7405	Intermediate Similarity	NPC150259
0.7399	Intermediate Similarity	NPC288074
0.7381	Intermediate Similarity	NPC475990
0.7381	Intermediate Similarity	NPC474880
0.7381	Intermediate Similarity	NPC221786
0.7355	Intermediate Similarity	NPC22079
0.7355	Intermediate Similarity	NPC475428
0.7353	Intermediate Similarity	NPC21174
0.7353	Intermediate Similarity	NPC472587
0.7353	Intermediate Similarity	NPC271797
0.7349	Intermediate Similarity	NPC141926
0.7341	Intermediate Similarity	NPC82331
0.7337	Intermediate Similarity	NPC229173
0.7329	Intermediate Similarity	NPC277157
0.7308	Intermediate Similarity	NPC179365
0.7301	Intermediate Similarity	NPC469525
0.7299	Intermediate Similarity	NPC64055
0.7294	Intermediate Similarity	NPC194881
0.729	Intermediate Similarity	NPC473587
0.7263	Intermediate Similarity	NPC108011
0.7262	Intermediate Similarity	NPC184476
0.7261	Intermediate Similarity	NPC473930
0.7233	Intermediate Similarity	NPC218268
0.7226	Intermediate Similarity	NPC473762
0.7225	Intermediate Similarity	NPC317430
0.7209	Intermediate Similarity	NPC274229
0.7208	Intermediate Similarity	NPC250361
0.7205	Intermediate Similarity	NPC73767
0.7202	Intermediate Similarity	NPC476219
0.7202	Intermediate Similarity	NPC38736
0.72	Intermediate Similarity	NPC477611
0.72	Intermediate Similarity	NPC472123
0.7195	Intermediate Similarity	NPC204141
0.7186	Intermediate Similarity	NPC470233
0.7184	Intermediate Similarity	NPC280548
0.7169	Intermediate Similarity	NPC187951
0.7169	Intermediate Similarity	NPC37548
0.7168	Intermediate Similarity	NPC478183
0.716	Intermediate Similarity	NPC469780
0.716	Intermediate Similarity	NPC469783
0.716	Intermediate Similarity	NPC469784
0.716	Intermediate Similarity	NPC238499
0.716	Intermediate Similarity	NPC469761
0.716	Intermediate Similarity	NPC469779
0.716	Intermediate Similarity	NPC469767
0.716	Intermediate Similarity	NPC115611
0.716	Intermediate Similarity	NPC469768
0.7152	Intermediate Similarity	NPC478186
0.7151	Intermediate Similarity	NPC162799
0.7151	Intermediate Similarity	NPC478182
0.7143	Intermediate Similarity	NPC232798
0.7143	Intermediate Similarity	NPC126492
0.7134	Intermediate Similarity	NPC282398
0.7126	Intermediate Similarity	NPC53947
0.7124	Intermediate Similarity	NPC46358
0.712	Intermediate Similarity	NPC243716
0.7119	Intermediate Similarity	NPC24594
0.7119	Intermediate Similarity	NPC472122
0.7118	Intermediate Similarity	NPC129721
0.7117	Intermediate Similarity	NPC469766
0.7114	Intermediate Similarity	NPC476566
0.7101	Intermediate Similarity	NPC470507
0.7101	Intermediate Similarity	NPC476297
0.7099	Intermediate Similarity	NPC110126
0.7091	Intermediate Similarity	NPC314372
0.7086	Intermediate Similarity	NPC474897
0.7086	Intermediate Similarity	NPC97343
0.7081	Intermediate Similarity	NPC84911
0.7079	Intermediate Similarity	NPC326575
0.7073	Intermediate Similarity	NPC190296
0.7066	Intermediate Similarity	NPC124005
0.7065	Intermediate Similarity	NPC231536
0.7059	Intermediate Similarity	NPC41174
0.7052	Intermediate Similarity	NPC149265
0.7048	Intermediate Similarity	NPC316069
0.7041	Intermediate Similarity	NPC281094
0.7041	Intermediate Similarity	NPC325903
0.703	Intermediate Similarity	NPC242556
0.7029	Intermediate Similarity	NPC201700
0.7029	Intermediate Similarity	NPC154293
0.7024	Intermediate Similarity	NPC24678
0.7024	Intermediate Similarity	NPC105818
0.7019	Intermediate Similarity	NPC96102
0.7019	Intermediate Similarity	NPC29886
0.7019	Intermediate Similarity	NPC261195
0.7018	Intermediate Similarity	NPC236711
0.7011	Intermediate Similarity	NPC17751
0.7011	Intermediate Similarity	NPC280864
0.7006	Intermediate Similarity	NPC201380
0.7006	Intermediate Similarity	NPC471294
0.7006	Intermediate Similarity	NPC161861
0.7006	Intermediate Similarity	NPC179787
0.7	Intermediate Similarity	NPC15840
0.7	Intermediate Similarity	NPC187827
0.7	Intermediate Similarity	NPC472105
0.6994	Remote Similarity	NPC16667
0.6994	Remote Similarity	NPC225018
0.6983	Remote Similarity	NPC151939
0.6983	Remote Similarity	NPC234987
0.6977	Remote Similarity	NPC293487
0.6975	Remote Similarity	NPC105127
0.6973	Remote Similarity	NPC329858
0.6964	Remote Similarity	NPC321911
0.6962	Remote Similarity	NPC475105
0.6962	Remote Similarity	NPC329896
0.6962	Remote Similarity	NPC475090
0.6961	Remote Similarity	NPC307191
0.6959	Remote Similarity	NPC285469
0.6954	Remote Similarity	NPC264580
0.6954	Remote Similarity	NPC469541
0.6951	Remote Similarity	NPC284635
0.6949	Remote Similarity	NPC201634
0.6946	Remote Similarity	NPC63545
0.6946	Remote Similarity	NPC288838
0.6946	Remote Similarity	NPC129042
0.6944	Remote Similarity	NPC133261
0.6941	Remote Similarity	NPC469763
0.6941	Remote Similarity	NPC469765
0.6941	Remote Similarity	NPC469760
0.6941	Remote Similarity	NPC259644
0.6941	Remote Similarity	NPC200214
0.6941	Remote Similarity	NPC73952
0.6941	Remote Similarity	NPC138842
0.6941	Remote Similarity	NPC469786
0.6941	Remote Similarity	NPC25008
0.6927	Remote Similarity	NPC56618
0.6927	Remote Similarity	NPC280852
0.6923	Remote Similarity	NPC472110
0.6923	Remote Similarity	NPC472108
0.6923	Remote Similarity	NPC143533
0.6923	Remote Similarity	NPC470205
0.6923	Remote Similarity	NPC139291
0.6923	Remote Similarity	NPC472109
0.6923	Remote Similarity	NPC472104
0.6919	Remote Similarity	NPC216643
0.6906	Remote Similarity	NPC300688
0.6905	Remote Similarity	NPC469811
0.6905	Remote Similarity	NPC471957
0.6903	Remote Similarity	NPC290094
0.6901	Remote Similarity	NPC80597
0.6901	Remote Similarity	NPC211572
0.6901	Remote Similarity	NPC75540

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 NPC6436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	692
0.2-0.3	1137
0.3-0.4	1941
0.4-0.5	2710
0.5-0.6	1833
0.6-0.7	422
0.7-0.8	62
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.816	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD3385	Approved
0.8037	Intermediate Similarity	NPD5315	Discontinued
0.8013	Intermediate Similarity	NPD5254	Discontinued
0.7988	Intermediate Similarity	NPD3323	Discontinued
0.7952	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1683	Approved
0.7857	Intermediate Similarity	NPD45	Approved
0.7857	Intermediate Similarity	NPD6554	Approved
0.7844	Intermediate Similarity	NPD4638	Approved
0.7844	Intermediate Similarity	NPD4640	Approved
0.7844	Intermediate Similarity	NPD4639	Approved
0.7834	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4181	Approved
0.7756	Intermediate Similarity	NPD2070	Approved
0.7756	Intermediate Similarity	NPD2071	Approved
0.7756	Intermediate Similarity	NPD2069	Approved
0.7756	Intermediate Similarity	NPD2068	Approved
0.7751	Intermediate Similarity	NPD3609	Approved
0.7751	Intermediate Similarity	NPD3610	Approved
0.7748	Intermediate Similarity	NPD3654	Approved
0.7707	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4547	Phase 3
0.7633	Intermediate Similarity	NPD5021	Discontinued
0.758	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD3505	Approved
0.7572	Intermediate Similarity	NPD3506	Approved
0.7546	Intermediate Similarity	NPD4462	Approved
0.7546	Intermediate Similarity	NPD4463	Approved
0.7529	Intermediate Similarity	NPD4079	Approved
0.7529	Intermediate Similarity	NPD4076	Approved
0.7514	Intermediate Similarity	NPD4075	Phase 2
0.747	Intermediate Similarity	NPD2150	Discontinued
0.7468	Intermediate Similarity	NPD3475	Approved
0.7468	Intermediate Similarity	NPD3476	Approved
0.7457	Intermediate Similarity	NPD4128	Approved
0.7444	Intermediate Similarity	NPD6281	Approved
0.7436	Intermediate Similarity	NPD4030	Approved
0.7436	Intermediate Similarity	NPD4028	Approved
0.7436	Intermediate Similarity	NPD4029	Approved
0.743	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4326	Phase 2
0.7386	Intermediate Similarity	NPD2119	Approved
0.7386	Intermediate Similarity	NPD2118	Approved
0.7372	Intermediate Similarity	NPD1994	Approved
0.7372	Intermediate Similarity	NPD1995	Approved
0.7372	Intermediate Similarity	NPD1993	Approved
0.7346	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1255	Approved
0.7342	Intermediate Similarity	NPD1254	Approved
0.7342	Intermediate Similarity	NPD1253	Approved
0.7342	Intermediate Similarity	NPD1256	Approved
0.7341	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1722	Approved
0.7325	Intermediate Similarity	NPD3942	Approved
0.7325	Intermediate Similarity	NPD3944	Approved
0.731	Intermediate Similarity	NPD2915	Discontinued
0.7308	Intermediate Similarity	NPD1251	Discontinued
0.7305	Intermediate Similarity	NPD6285	Phase 2
0.7289	Intermediate Similarity	NPD2882	Phase 1
0.7284	Intermediate Similarity	NPD4047	Discontinued
0.7273	Intermediate Similarity	NPD1183	Approved
0.7273	Intermediate Similarity	NPD3100	Discontinued
0.7239	Intermediate Similarity	NPD4509	Discontinued
0.7222	Intermediate Similarity	NPD5020	Approved
0.7205	Intermediate Similarity	NPD786	Approved
0.7188	Intermediate Similarity	NPD1262	Discovery
0.7186	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6158	Phase 2
0.7179	Intermediate Similarity	NPD947	Approved
0.7178	Intermediate Similarity	NPD2006	Phase 2
0.7169	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2430	Phase 2
0.7143	Intermediate Similarity	NPD2837	Discontinued
0.7143	Intermediate Similarity	NPD3961	Discontinued
0.7128	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2640	Approved
0.7126	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2641	Approved
0.7126	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6664	Approved
0.7095	Intermediate Similarity	NPD5473	Discontinued
0.7072	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4880	Discontinued
0.7059	Intermediate Similarity	NPD2580	Discontinued
0.7041	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2172	Phase 1
0.7022	Intermediate Similarity	NPD5104	Approved
0.7019	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4902	Discontinued
0.6994	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1326	Approved
0.6989	Remote Similarity	NPD1325	Approved
0.6983	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5065	Approved
0.6959	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3583	Phase 2
0.6946	Remote Similarity	NPD7469	Discontinued
0.6946	Remote Similarity	NPD7717	Approved
0.6946	Remote Similarity	NPD7716	Approved
0.694	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD977	Approved
0.6901	Remote Similarity	NPD976	Approved
0.6901	Remote Similarity	NPD975	Approved
0.6893	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2075	Approved
0.689	Remote Similarity	NPD2072	Approved
0.689	Remote Similarity	NPD2074	Approved
0.689	Remote Similarity	NPD2073	Approved
0.6889	Remote Similarity	NPD7111	Discontinued
0.6885	Remote Similarity	NPD4957	Phase 2
0.6883	Remote Similarity	NPD271	Approved
0.6883	Remote Similarity	NPD268	Approved
0.6883	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5075	Discontinued
0.6848	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1404	Approved
0.6839	Remote Similarity	NPD1403	Approved
0.6839	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7671	Approved
0.6837	Remote Similarity	NPD7672	Approved
0.6836	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD991	Phase 2
0.6835	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3320	Approved
0.6831	Remote Similarity	NPD3318	Approved
0.6831	Remote Similarity	NPD3319	Phase 1
0.6818	Remote Similarity	NPD2720	Phase 1
0.6818	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2840	Approved
0.6811	Remote Similarity	NPD5809	Phase 3
0.6805	Remote Similarity	NPD4703	Approved
0.6805	Remote Similarity	NPD4702	Approved
0.6798	Remote Similarity	NPD5436	Phase 1
0.6796	Remote Similarity	NPD2144	Approved
0.6796	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4499	Approved
0.678	Remote Similarity	NPD2639	Approved
0.678	Remote Similarity	NPD2642	Approved
0.6778	Remote Similarity	NPD3799	Suspended
0.6776	Remote Similarity	NPD3038	Discontinued
0.6774	Remote Similarity	NPD2383	Phase 1
0.6774	Remote Similarity	NPD8431	Approved
0.6774	Remote Similarity	NPD7394	Phase 2
0.676	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6828	Phase 2
0.6757	Remote Similarity	NPD6227	Discontinued
0.6743	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.674	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7233	Approved
0.6738	Remote Similarity	NPD7234	Approved
0.6731	Remote Similarity	NPD5787	Discontinued
0.6726	Remote Similarity	NPD5671	Approved
0.6724	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1002	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD509	Phase 3
0.672	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6991	Approved
0.6717	Remote Similarity	NPD4520	Approved
0.6708	Remote Similarity	NPD715	Phase 3
0.6706	Remote Similarity	NPD1661	Suspended
0.6703	Remote Similarity	NPD5892	Approved
0.6702	Remote Similarity	NPD7935	Phase 2
0.6701	Remote Similarity	NPD4142	Discontinued
0.6698	Remote Similarity	NPD5891	Approved
0.6685	Remote Similarity	NPD6794	Approved
0.6685	Remote Similarity	NPD7006	Approved
0.6685	Remote Similarity	NPD4399	Phase 2
0.6684	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3112	Approved
0.6667	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3115	Approved
0.6667	Remote Similarity	NPD3113	Approved
0.6667	Remote Similarity	NPD3114	Approved
0.6649	Remote Similarity	NPD4601	Approved
0.6649	Remote Similarity	NPD5105	Approved
0.6649	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4600	Approved
0.6649	Remote Similarity	NPD5106	Approved
0.6648	Remote Similarity	NPD2380	Approved
0.6648	Remote Similarity	NPD2382	Approved
0.6648	Remote Similarity	NPD2381	Approved
0.6648	Remote Similarity	NPD5862	Discovery
0.6648	Remote Similarity	NPD5100	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