NPASS Compound

Structure

NPC291583 OpenBabel07101718312D 37 39 0 0 0 0 0 0 0 0999 V2000 2.6228 -4.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 -4.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7383 -5.3311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8222 -6.0826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 1.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5549 -2.4040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 1.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8622 0.1495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2209 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6900 -4.2807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -2.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 -3.5291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -3.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6928 -4.3554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -2.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9944 -1.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 -2.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -4.4010 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2589 -5.2564 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 0.0990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9916 -1.5777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 1.0990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8650 0.0747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 -1.9010 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -2.1238 -3.3797 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -2.0245 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 0.2225 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 32 1 0 0 0 0 9 33 1 0 0 0 0 10 34 1 0 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 17 29 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 18 30 1 0 0 0 0 19 25 1 0 0 0 0 19 31 1 0 0 0 0 20 26 1 0 0 0 0 20 32 1 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 25 2 0 0 0 0 23 35 1 0 0 0 0 24 26 2 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 26 37 1 0 0 0 0 36 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	602.14
Volume:	566.463
LogP:	5.591
LogD:	4.167
LogS:	-6.169
# Rotatable Bonds:	12
TPSA:	43.4
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.162
Synthetic Accessibility Score:	3.743
Fsp3:	0.538
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.025
MDCK Permeability:	2.022520493483171e-05
Pgp-inhibitor:	0.412
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.476
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.442
Plasma Protein Binding (PPB):	95.96394348144531%
Volume Distribution (VD):	1.378
Pgp-substrate:	2.811563491821289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.462
CYP1A2-substrate:	0.992
CYP2C19-inhibitor:	0.332
CYP2C19-substrate:	0.992
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.069
CYP2D6-substrate:	0.949
CYP3A4-inhibitor:	0.443
CYP3A4-substrate:	0.957

ADMET: Excretion

Clearance (CL):	7.081
Half-life (T1/2):	0.017

ADMET: Toxicity

hERG Blockers:	0.832
Human Hepatotoxicity (H-HT):	0.156
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.978
Maximum Recommended Daily Dose:	0.08
Skin Sensitization:	0.206
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC291583

Natural Product ID:	NPC291583
*Common Name:**	Lissoclinotoxin F
IUPAC Name:	2-[1-[2-(dimethylamino)ethyl]-3,4,7,8-tetramethoxy-2,9-bis(methylsulfanyl)benzo[c][1,2,5]benzotrithiepin-10-yl]-N,N-dimethylethanamine
Synonyms:	Lissoclinotoxin F
Standard InCHIKey:	DNJBHFLCTDTJMS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H38N2O4S5/c1-27(2)13-11-15-21(33-9)17(29-5)19(31-7)25-23(15)35-24-16(12-14-28(3)4)22(34-10)18(30-6)20(32-8)26(24)37-36-25/h11-14H2,1-10H3
SMILES:	CN(C)CCc1c(c(c(c2c1sc1c(CCN(C)C)c(c(c(c1ss2)OC)OC)SC)OC)OC)SC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL375614
PubChem CID:	10077362
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines

*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
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[17269824]
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18977148]
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28181805]

☑ 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
EC50	1
IC50	3
Others	2

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3171	Cell Line	V79	Cricetulus griseus	IC50	=	280.0	nM	PMID[550549]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	230.0	nM	PMID[550549]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	=	4.2	ug.mL-1	PMID[550549]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	IZ	=	18.0	mm	PMID[550548]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	IZ	=	10.5	mm	PMID[550548]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	280.0	nM	PMID[550548]

☑ 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 NPC291583 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	413
0.1-0.2	4302
0.2-0.3	14907
0.3-0.4	8389
0.4-0.5	12095
0.5-0.6	2458
0.6-0.7	113
0.7-0.8	7
0.8-0.85	2
0.85-0.9	4
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC191200
0.9658	High Similarity	NPC28414
0.9658	High Similarity	NPC298924
0.9467	High Similarity	NPC257143
0.9444	High Similarity	NPC226601
0.9178	High Similarity	NPC69623
0.9172	High Similarity	NPC177023
0.8805	High Similarity	NPC130921
0.8726	High Similarity	NPC94292
0.8411	Intermediate Similarity	NPC261940
0.8239	Intermediate Similarity	NPC131440
0.8025	Intermediate Similarity	NPC296858
0.7857	Intermediate Similarity	NPC59661
0.7821	Intermediate Similarity	NPC474553
0.7532	Intermediate Similarity	NPC475698
0.7453	Intermediate Similarity	NPC474649
0.7453	Intermediate Similarity	NPC474652
0.6894	Remote Similarity	NPC167944
0.6894	Remote Similarity	NPC231884
0.6894	Remote Similarity	NPC42793
0.6815	Remote Similarity	NPC172403
0.6728	Remote Similarity	NPC11147
0.6627	Remote Similarity	NPC323204
0.6603	Remote Similarity	NPC298486
0.6592	Remote Similarity	NPC206941
0.659	Remote Similarity	NPC206372
0.659	Remote Similarity	NPC203424
0.6543	Remote Similarity	NPC118419
0.6541	Remote Similarity	NPC301713
0.6527	Remote Similarity	NPC328750
0.6527	Remote Similarity	NPC213206
0.6527	Remote Similarity	NPC474915
0.6527	Remote Similarity	NPC188163
0.6522	Remote Similarity	NPC160193
0.6467	Remote Similarity	NPC314682
0.645	Remote Similarity	NPC136860
0.645	Remote Similarity	NPC128019
0.645	Remote Similarity	NPC476567
0.6442	Remote Similarity	NPC214869
0.6433	Remote Similarity	NPC473934
0.638	Remote Similarity	NPC114102
0.638	Remote Similarity	NPC476570
0.6347	Remote Similarity	NPC193528
0.6323	Remote Similarity	NPC120075
0.6319	Remote Similarity	NPC35961
0.6319	Remote Similarity	NPC52029
0.6319	Remote Similarity	NPC195749
0.6319	Remote Similarity	NPC262641
0.6301	Remote Similarity	NPC210437
0.6301	Remote Similarity	NPC51957
0.6301	Remote Similarity	NPC106295
0.6301	Remote Similarity	NPC16107
0.6301	Remote Similarity	NPC476144
0.629	Remote Similarity	NPC20395
0.6279	Remote Similarity	NPC185838
0.6279	Remote Similarity	NPC145304
0.6264	Remote Similarity	NPC476571
0.6264	Remote Similarity	NPC135538
0.6264	Remote Similarity	NPC147390
0.6264	Remote Similarity	NPC7467
0.6264	Remote Similarity	NPC428
0.6264	Remote Similarity	NPC475959
0.6264	Remote Similarity	NPC24233
0.6264	Remote Similarity	NPC246587
0.6264	Remote Similarity	NPC130941
0.6258	Remote Similarity	NPC155838
0.6236	Remote Similarity	NPC80129
0.6236	Remote Similarity	NPC187022
0.6229	Remote Similarity	NPC211296
0.6207	Remote Similarity	NPC191376
0.6207	Remote Similarity	NPC179825
0.6207	Remote Similarity	NPC321505
0.6207	Remote Similarity	NPC476151
0.6205	Remote Similarity	NPC160692
0.6201	Remote Similarity	NPC25084
0.6201	Remote Similarity	NPC247639
0.6196	Remote Similarity	NPC153990
0.6196	Remote Similarity	NPC251571
0.6196	Remote Similarity	NPC186898
0.6193	Remote Similarity	NPC13397
0.6193	Remote Similarity	NPC88249
0.6193	Remote Similarity	NPC151895
0.6193	Remote Similarity	NPC220858
0.6193	Remote Similarity	NPC97221
0.6193	Remote Similarity	NPC192768
0.619	Remote Similarity	NPC131204
0.619	Remote Similarity	NPC7018
0.619	Remote Similarity	NPC301050
0.619	Remote Similarity	NPC416184
0.6185	Remote Similarity	NPC110337
0.618	Remote Similarity	NPC475557
0.6169	Remote Similarity	NPC165106
0.6158	Remote Similarity	NPC476568
0.6154	Remote Similarity	NPC312770
0.6154	Remote Similarity	NPC160607
0.6154	Remote Similarity	NPC9341
0.6154	Remote Similarity	NPC14600
0.6154	Remote Similarity	NPC204848
0.6154	Remote Similarity	NPC81067
0.6154	Remote Similarity	NPC41473
0.6154	Remote Similarity	NPC253429
0.6136	Remote Similarity	NPC219162
0.6136	Remote Similarity	NPC103379
0.6136	Remote Similarity	NPC477565
0.6136	Remote Similarity	NPC92541
0.6133	Remote Similarity	NPC216816
0.6133	Remote Similarity	NPC186595
0.6131	Remote Similarity	NPC475828
0.6124	Remote Similarity	NPC233029
0.6124	Remote Similarity	NPC210148
0.6118	Remote Similarity	NPC210086
0.6118	Remote Similarity	NPC299583
0.6111	Remote Similarity	NPC105513
0.6108	Remote Similarity	NPC313737
0.6108	Remote Similarity	NPC6854
0.6108	Remote Similarity	NPC285078
0.6105	Remote Similarity	NPC100478
0.6105	Remote Similarity	NPC222039
0.6101	Remote Similarity	NPC321133
0.6099	Remote Similarity	NPC46067
0.6092	Remote Similarity	NPC130926
0.6092	Remote Similarity	NPC5462
0.609	Remote Similarity	NPC475815
0.609	Remote Similarity	NPC473264
0.609	Remote Similarity	NPC47194
0.6089	Remote Similarity	NPC292003
0.6067	Remote Similarity	NPC81733
0.6067	Remote Similarity	NPC8337
0.6067	Remote Similarity	NPC85747
0.6067	Remote Similarity	NPC326316
0.6056	Remote Similarity	NPC172765
0.6056	Remote Similarity	NPC189266
0.6056	Remote Similarity	NPC469817
0.6056	Remote Similarity	NPC193949
0.6056	Remote Similarity	NPC2413
0.6056	Remote Similarity	NPC39701
0.6056	Remote Similarity	NPC278799
0.6056	Remote Similarity	NPC207757
0.6056	Remote Similarity	NPC93593
0.6056	Remote Similarity	NPC110416
0.6056	Remote Similarity	NPC244112
0.6056	Remote Similarity	NPC184026
0.6056	Remote Similarity	NPC276588
0.6056	Remote Similarity	NPC54379
0.6056	Remote Similarity	NPC5238
0.6056	Remote Similarity	NPC204828
0.6056	Remote Similarity	NPC325871
0.6056	Remote Similarity	NPC127674
0.6056	Remote Similarity	NPC216459
0.6056	Remote Similarity	NPC41178
0.6056	Remote Similarity	NPC295691
0.6056	Remote Similarity	NPC249797
0.6056	Remote Similarity	NPC99659
0.6056	Remote Similarity	NPC138487
0.6049	Remote Similarity	NPC13020
0.6049	Remote Similarity	NPC140359
0.6048	Remote Similarity	NPC130595
0.6048	Remote Similarity	NPC93882
0.6045	Remote Similarity	NPC60538
0.6045	Remote Similarity	NPC207824
0.6038	Remote Similarity	NPC474320
0.6034	Remote Similarity	NPC114124
0.6033	Remote Similarity	NPC475393
0.6025	Remote Similarity	NPC211992
0.6023	Remote Similarity	NPC277857
0.6023	Remote Similarity	NPC144863
0.6023	Remote Similarity	NPC115144
0.6023	Remote Similarity	NPC296898
0.6023	Remote Similarity	NPC231572
0.6023	Remote Similarity	NPC253883
0.6023	Remote Similarity	NPC95075
0.6023	Remote Similarity	NPC90844
0.6022	Remote Similarity	NPC186063
0.6022	Remote Similarity	NPC146288
0.6	Remote Similarity	NPC4138
0.6	Remote Similarity	NPC121275
0.6	Remote Similarity	NPC284183
0.6	Remote Similarity	NPC291847
0.5989	Remote Similarity	NPC476572
0.5989	Remote Similarity	NPC129603
0.5978	Remote Similarity	NPC277669
0.5978	Remote Similarity	NPC476579
0.5978	Remote Similarity	NPC76213
0.5976	Remote Similarity	NPC218530
0.5975	Remote Similarity	NPC474214
0.5975	Remote Similarity	NPC474040
0.5975	Remote Similarity	NPC470626
0.5968	Remote Similarity	NPC317272
0.5968	Remote Similarity	NPC42549
0.5968	Remote Similarity	NPC240841
0.5968	Remote Similarity	NPC268503
0.5968	Remote Similarity	NPC256012
0.5968	Remote Similarity	NPC250846
0.5965	Remote Similarity	NPC252107
0.5965	Remote Similarity	NPC220923
0.5956	Remote Similarity	NPC111485
0.5944	Remote Similarity	NPC476580
0.5944	Remote Similarity	NPC275027
0.5938	Remote Similarity	NPC254625
0.5938	Remote Similarity	NPC475961

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 NPC291583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	1119
0.2-0.3	1971
0.3-0.4	3292
0.4-0.5	1915
0.5-0.6	564
0.6-0.7	51
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7299	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5718	Phase 2
0.6987	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7802	Discontinued
0.6894	Remote Similarity	NPD6896	Approved
0.6894	Remote Similarity	NPD6895	Approved
0.6667	Remote Similarity	NPD5085	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4180	Approved
0.659	Remote Similarity	NPD4179	Approved
0.6568	Remote Similarity	NPD7124	Phase 2
0.6532	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6875	Approved
0.6494	Remote Similarity	NPD6876	Approved
0.6484	Remote Similarity	NPD730	Discontinued
0.6457	Remote Similarity	NPD1757	Discontinued
0.6457	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7110	Phase 1
0.6455	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1642	Discontinued
0.6395	Remote Similarity	NPD4739	Approved
0.6391	Remote Similarity	NPD3060	Approved
0.6391	Remote Similarity	NPD4162	Approved
0.6384	Remote Similarity	NPD487	Discontinued
0.6358	Remote Similarity	NPD2236	Approved
0.6335	Remote Similarity	NPD7905	Discontinued
0.6316	Remote Similarity	NPD5241	Discontinued
0.6301	Remote Similarity	NPD4584	Approved
0.6279	Remote Similarity	NPD6066	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD7298	Approved
0.6228	Remote Similarity	NPD2653	Approved
0.6222	Remote Similarity	NPD3075	Approved
0.6221	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6111	Discontinued
0.6185	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD6890	Discontinued
0.6169	Remote Similarity	NPD5283	Phase 1
0.6163	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD746	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5720	Discontinued
0.6136	Remote Similarity	NPD6030	Approved
0.6136	Remote Similarity	NPD6031	Approved
0.6127	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.612	Remote Similarity	NPD2644	Approved
0.6114	Remote Similarity	NPD6322	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD4123	Phase 3
0.6111	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2922	Phase 1
0.6105	Remote Similarity	NPD4236	Phase 3
0.6105	Remote Similarity	NPD4237	Approved
0.6101	Remote Similarity	NPD2667	Approved
0.6101	Remote Similarity	NPD2668	Approved
0.6094	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD6873	Phase 2
0.6087	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4017	Approved
0.6048	Remote Similarity	NPD2674	Phase 3
0.6022	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD5177	Phase 3
0.6	Remote Similarity	NPD6385	Approved
0.6	Remote Similarity	NPD6386	Approved
0.5989	Remote Similarity	NPD7015	Phase 2
0.5989	Remote Similarity	NPD7016	Phase 3
0.5989	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD5111	Phase 2
0.5988	Remote Similarity	NPD5109	Approved
0.5988	Remote Similarity	NPD5110	Phase 2
0.5977	Remote Similarity	NPD6331	Phase 2
0.5967	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD6788	Approved
0.5955	Remote Similarity	NPD2900	Approved
0.5955	Remote Similarity	NPD3639	Approved
0.5955	Remote Similarity	NPD3640	Phase 3
0.5955	Remote Similarity	NPD3641	Approved
0.5955	Remote Similarity	NPD2901	Approved
0.5954	Remote Similarity	NPD7153	Discontinued
0.5944	Remote Similarity	NPD4675	Approved
0.5944	Remote Similarity	NPD4678	Approved
0.5934	Remote Similarity	NPD5772	Approved
0.5934	Remote Similarity	NPD2978	Approved
0.5934	Remote Similarity	NPD2977	Approved
0.5934	Remote Similarity	NPD5773	Approved
0.5932	Remote Similarity	NPD1424	Approved
0.5924	Remote Similarity	NPD7833	Phase 2
0.5924	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD7831	Phase 2
0.5922	Remote Similarity	NPD4210	Discontinued
0.5917	Remote Similarity	NPD4101	Phase 1
0.5915	Remote Similarity	NPD5310	Approved
0.5915	Remote Similarity	NPD5311	Approved
0.5915	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD4773	Phase 2
0.5912	Remote Similarity	NPD4772	Phase 2
0.5902	Remote Similarity	NPD2560	Approved
0.5902	Remote Similarity	NPD2563	Approved
0.5896	Remote Similarity	NPD1803	Phase 3
0.5893	Remote Similarity	NPD3145	Approved
0.5893	Remote Similarity	NPD3144	Approved
0.589	Remote Similarity	NPD2230	Approved
0.589	Remote Similarity	NPD2232	Approved
0.589	Remote Similarity	NPD2233	Approved
0.5889	Remote Similarity	NPD6813	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6071	Discontinued
0.5876	Remote Similarity	NPD3124	Discontinued
0.5872	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.586	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.5858	Remote Similarity	NPD3532	Approved
0.5858	Remote Similarity	NPD3531	Approved
0.5858	Remote Similarity	NPD3530	Approved
0.5854	Remote Similarity	NPD1669	Approved
0.5848	Remote Similarity	NPD2492	Phase 1
0.5847	Remote Similarity	NPD6064	Phase 1
0.5847	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD8251	Approved
0.5842	Remote Similarity	NPD8252	Approved
0.5842	Remote Similarity	NPD8099	Discontinued
0.5839	Remote Similarity	NPD3444	Approved
0.5839	Remote Similarity	NPD3443	Approved
0.5839	Remote Similarity	NPD3445	Approved
0.5838	Remote Similarity	NPD3539	Phase 1
0.5838	Remote Similarity	NPD2161	Phase 2
0.5833	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD3686	Approved
0.5833	Remote Similarity	NPD3687	Approved
0.5829	Remote Similarity	NPD6107	Approved
0.5824	Remote Similarity	NPD2238	Phase 2
0.5813	Remote Similarity	NPD5536	Phase 2
0.5812	Remote Similarity	NPD8156	Discontinued
0.5805	Remote Similarity	NPD3540	Phase 1
0.5805	Remote Similarity	NPD1375	Discontinued
0.5801	Remote Similarity	NPD4005	Discontinued
0.58	Remote Similarity	NPD6493	Phase 3
0.5799	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD4010	Discontinued
0.5795	Remote Similarity	NPD4483	Discontinued
0.5783	Remote Similarity	NPD3055	Approved
0.5783	Remote Similarity	NPD4098	Discontinued
0.5783	Remote Similarity	NPD3053	Approved
0.578	Remote Similarity	NPD3152	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD2486	Discontinued
0.5775	Remote Similarity	NPD5677	Discontinued
0.5767	Remote Similarity	NPD6687	Approved
0.5767	Remote Similarity	NPD6688	Approved
0.5767	Remote Similarity	NPD3294	Phase 2
0.5765	Remote Similarity	NPD2245	Discovery
0.5761	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.5756	Remote Similarity	NPD5314	Approved
0.5756	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.5754	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD5604	Discontinued
0.5751	Remote Similarity	NPD2759	Clinical (unspecified phase)
0.575	Remote Similarity	NPD3596	Phase 2
0.5749	Remote Similarity	NPD6584	Phase 3
0.5743	Remote Similarity	NPD5564	Approved
0.5741	Remote Similarity	NPD6382	Discontinued
0.5741	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD3599	Approved
0.5731	Remote Similarity	NPD3110	Approved
0.5731	Remote Similarity	NPD3109	Approved
0.573	Remote Similarity	NPD5978	Approved
0.573	Remote Similarity	NPD5977	Approved
0.5722	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD7526	Approved
0.5722	Remote Similarity	NPD52	Approved
0.5707	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD3657	Discovery
0.5698	Remote Similarity	NPD5297	Approved
0.5691	Remote Similarity	NPD5976	Discontinued
0.5684	Remote Similarity	NPD4083	Discontinued
0.5679	Remote Similarity	NPD6581	Approved
0.5679	Remote Similarity	NPD6580	Approved
0.5676	Remote Similarity	NPD4585	Approved
0.5673	Remote Similarity	NPD4475	Approved
0.5673	Remote Similarity	NPD4474	Approved
0.567	Remote Similarity	NPD6297	Approved
0.5668	Remote Similarity	NPD4055	Discovery
0.5665	Remote Similarity	NPD7034	Discontinued
0.5663	Remote Similarity	NPD1421	Approved
0.5663	Remote Similarity	NPD1420	Approved
0.5663	Remote Similarity	NPD2428	Approved
0.5663	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD7280	Phase 3
0.5663	Remote Similarity	NPD7281	Phase 3
0.5663	Remote Similarity	NPD2429	Approved
0.5654	Remote Similarity	NPD8015	Phase 3
0.5654	Remote Similarity	NPD4481	Phase 3
0.5648	Remote Similarity	NPD5313	Approved

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