NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.17
Volume:	274.851
LogP:	2.741
LogD:	2.617
LogS:	-4.108
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.658
Synthetic Accessibility Score:	4.445
Fsp3:	0.933
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:	-4.708
MDCK Permeability:	2.567010415077675e-05
Pgp-inhibitor:	0.412
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.408
Plasma Protein Binding (PPB):	68.99034881591797%
Volume Distribution (VD):	1.46
Pgp-substrate:	39.25129318237305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.603
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.077
CYP2C9-substrate:	0.635
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.461
CYP3A4-inhibitor:	0.129
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	5.722
Half-life (T1/2):	0.275

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.075
AMES Toxicity:	0.87
Rat Oral Acute Toxicity:	0.533
Maximum Recommended Daily Dose:	0.206
Skin Sensitization:	0.551
Carcinogencity:	0.605
Eye Corrosion:	0.038
Eye Irritation:	0.323
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC79308

Natural Product ID:	NPC79308
*Common Name:**	Dendocarbin D
IUPAC Name:	(1R,3aR,5aS,9aS,9bR)-1,3a-dihydroxy-6,6,9a-trimethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[e][2]benzofuran-3-one
Synonyms:	Dendocarbin D
Standard InCHIKey:	GGWKVMGHNXNHGX-MTLGCJRHSA-N
Standard InCHI:	InChI=1S/C15H24O4/c1-13(2)6-4-7-14(3)9(13)5-8-15(18)10(14)11(16)19-12(15)17/h9-11,16,18H,4-8H2,1-3H3/t9-,10+,11+,14-,15+/m0/s1
SMILES:	O[C@@H]1OC(=O)[C@@]2([C@H]1[C@@]1(C)CCCC([C@@H]1CC2)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512506
PubChem CID:	11129314
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO8660	Dendrodoris carbunculosa	Species	Dendrodorididae	Eukaryota	n.a.	Amatsu-kominato, Boso Peninsula, central Japan (35 07N, 140 11E)	1999-NOV	PMID[11421732]
NPO7781	Piper scutifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18031016]
NPO6857	Actinidia eriantha	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO578	Eriope blanchetii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2429	Gracilariopsis lemaneiformis	Species	Gracilariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7781	Piper scutifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7474	Sicya macularia	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7919	Hedysarum sericeum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5987	Hypericum yojiroanum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6857	Actinidia eriantha	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1548	Nardia succulenta	Species	Solenostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24628	Lamium galeobdolon	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5268	Chenopodium hircinum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8660	Dendrodoris carbunculosa	Species	Dendrodorididae	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	15.0	ug.mL-1	PMID[462960]
NPT168	Cell Line	P388	Mus musculus	IC50	=	16.0	ug.mL-1	PMID[462960]
NPT168	Cell Line	P388	Mus musculus	IC50	=	14.0	ug.mL-1	PMID[462960]

☑ 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 NPC79308 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	360
0.1-0.2	2883
0.2-0.3	9071
0.3-0.4	13650
0.4-0.5	6463
0.5-0.6	5781
0.6-0.7	4036
0.7-0.8	444
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8625	High Similarity	NPC307865
0.8462	Intermediate Similarity	NPC470632
0.8462	Intermediate Similarity	NPC74466
0.8152	Intermediate Similarity	NPC475785
0.814	Intermediate Similarity	NPC18953
0.8132	Intermediate Similarity	NPC309127
0.8132	Intermediate Similarity	NPC247877
0.8046	Intermediate Similarity	NPC477445
0.8	Intermediate Similarity	NPC475743
0.7978	Intermediate Similarity	NPC221993
0.7978	Intermediate Similarity	NPC33398
0.7978	Intermediate Similarity	NPC471221
0.7957	Intermediate Similarity	NPC475765
0.7955	Intermediate Similarity	NPC92139
0.7955	Intermediate Similarity	NPC471411
0.7955	Intermediate Similarity	NPC471410
0.7912	Intermediate Similarity	NPC475878
0.7901	Intermediate Similarity	NPC109510
0.7865	Intermediate Similarity	NPC62202
0.7865	Intermediate Similarity	NPC213658
0.7865	Intermediate Similarity	NPC45833
0.7865	Intermediate Similarity	NPC110365
0.7841	Intermediate Similarity	NPC478111
0.7826	Intermediate Similarity	NPC475307
0.7816	Intermediate Similarity	NPC15091
0.7802	Intermediate Similarity	NPC50443
0.7802	Intermediate Similarity	NPC18536
0.7791	Intermediate Similarity	NPC271572
0.7791	Intermediate Similarity	NPC474870
0.7778	Intermediate Similarity	NPC476435
0.7778	Intermediate Similarity	NPC203974
0.7765	Intermediate Similarity	NPC474754
0.7727	Intermediate Similarity	NPC473299
0.7708	Intermediate Similarity	NPC80417
0.7692	Intermediate Similarity	NPC253618
0.7692	Intermediate Similarity	NPC477440
0.7692	Intermediate Similarity	NPC477443
0.7692	Intermediate Similarity	NPC77001
0.7684	Intermediate Similarity	NPC472273
0.7683	Intermediate Similarity	NPC474755
0.7674	Intermediate Similarity	NPC472943
0.7674	Intermediate Similarity	NPC60568
0.7674	Intermediate Similarity	NPC186588
0.7674	Intermediate Similarity	NPC472951
0.7634	Intermediate Similarity	NPC472148
0.7634	Intermediate Similarity	NPC472147
0.7624	Intermediate Similarity	NPC236753
0.7624	Intermediate Similarity	NPC228190
0.7609	Intermediate Similarity	NPC472146
0.7609	Intermediate Similarity	NPC477442
0.7609	Intermediate Similarity	NPC470114
0.7609	Intermediate Similarity	NPC477433
0.7609	Intermediate Similarity	NPC477444
0.7609	Intermediate Similarity	NPC185529
0.7604	Intermediate Similarity	NPC472144
0.7604	Intermediate Similarity	NPC253995
0.7595	Intermediate Similarity	NPC84562
0.759	Intermediate Similarity	NPC317212
0.759	Intermediate Similarity	NPC55508
0.7586	Intermediate Similarity	NPC470156
0.7586	Intermediate Similarity	NPC48756
0.7586	Intermediate Similarity	NPC58631
0.7586	Intermediate Similarity	NPC280781
0.7582	Intermediate Similarity	NPC470872
0.7582	Intermediate Similarity	NPC476379
0.7579	Intermediate Similarity	NPC116683
0.7579	Intermediate Similarity	NPC193785
0.7576	Intermediate Similarity	NPC88469
0.7553	Intermediate Similarity	NPC206878
0.7551	Intermediate Similarity	NPC80640
0.7528	Intermediate Similarity	NPC477434
0.7528	Intermediate Similarity	NPC65133
0.7525	Intermediate Similarity	NPC207693
0.75	Intermediate Similarity	NPC476928
0.75	Intermediate Similarity	NPC477447
0.75	Intermediate Similarity	NPC477446
0.75	Intermediate Similarity	NPC164289
0.75	Intermediate Similarity	NPC472145
0.75	Intermediate Similarity	NPC311642
0.75	Intermediate Similarity	NPC471241
0.75	Intermediate Similarity	NPC41542
0.75	Intermediate Similarity	NPC242771
0.75	Intermediate Similarity	NPC100366
0.75	Intermediate Similarity	NPC208912
0.75	Intermediate Similarity	NPC2096
0.75	Intermediate Similarity	NPC470155
0.7474	Intermediate Similarity	NPC215570
0.7473	Intermediate Similarity	NPC470920
0.7471	Intermediate Similarity	NPC471216
0.7471	Intermediate Similarity	NPC471217
0.7451	Intermediate Similarity	NPC208333
0.7451	Intermediate Similarity	NPC227879
0.7451	Intermediate Similarity	NPC22709
0.7447	Intermediate Similarity	NPC472232
0.7447	Intermediate Similarity	NPC472231
0.7444	Intermediate Similarity	NPC235402
0.7444	Intermediate Similarity	NPC476715
0.7442	Intermediate Similarity	NPC252483
0.7442	Intermediate Similarity	NPC191345
0.7426	Intermediate Similarity	NPC126753
0.7423	Intermediate Similarity	NPC211087
0.7416	Intermediate Similarity	NPC474346
0.7416	Intermediate Similarity	NPC259173
0.7416	Intermediate Similarity	NPC213737
0.7416	Intermediate Similarity	NPC474253
0.7416	Intermediate Similarity	NPC474284
0.7416	Intermediate Similarity	NPC475820
0.7412	Intermediate Similarity	NPC107963
0.74	Intermediate Similarity	NPC267637
0.74	Intermediate Similarity	NPC100078
0.7396	Intermediate Similarity	NPC476728
0.7396	Intermediate Similarity	NPC235109
0.7386	Intermediate Similarity	NPC470154
0.7386	Intermediate Similarity	NPC12933
0.7386	Intermediate Similarity	NPC209318
0.7386	Intermediate Similarity	NPC71541
0.7386	Intermediate Similarity	NPC223330
0.7381	Intermediate Similarity	NPC472944
0.7381	Intermediate Similarity	NPC472945
0.7379	Intermediate Similarity	NPC470622
0.7374	Intermediate Similarity	NPC471254
0.7374	Intermediate Similarity	NPC213528
0.7374	Intermediate Similarity	NPC244969
0.7368	Intermediate Similarity	NPC470424
0.7363	Intermediate Similarity	NPC120395
0.7363	Intermediate Similarity	NPC474008
0.7363	Intermediate Similarity	NPC248216
0.7356	Intermediate Similarity	NPC275243
0.7353	Intermediate Similarity	NPC472079
0.7347	Intermediate Similarity	NPC477655
0.734	Intermediate Similarity	NPC474065
0.734	Intermediate Similarity	NPC216137
0.7333	Intermediate Similarity	NPC34984
0.7333	Intermediate Similarity	NPC105895
0.7333	Intermediate Similarity	NPC475689
0.7333	Intermediate Similarity	NPC25037
0.7333	Intermediate Similarity	NPC291310
0.7327	Intermediate Similarity	NPC184805
0.7327	Intermediate Similarity	NPC273189
0.7327	Intermediate Similarity	NPC166079
0.7326	Intermediate Similarity	NPC143250
0.7326	Intermediate Similarity	NPC207010
0.7326	Intermediate Similarity	NPC317913
0.732	Intermediate Similarity	NPC266417
0.7312	Intermediate Similarity	NPC194642
0.7308	Intermediate Similarity	NPC473062
0.7308	Intermediate Similarity	NPC306750
0.7303	Intermediate Similarity	NPC121121
0.7303	Intermediate Similarity	NPC102156
0.7303	Intermediate Similarity	NPC477936
0.7303	Intermediate Similarity	NPC477935
0.7303	Intermediate Similarity	NPC148740
0.73	Intermediate Similarity	NPC471253
0.73	Intermediate Similarity	NPC34562
0.7292	Intermediate Similarity	NPC470031
0.7292	Intermediate Similarity	NPC82633
0.729	Intermediate Similarity	NPC179429
0.7283	Intermediate Similarity	NPC252714
0.7283	Intermediate Similarity	NPC239938
0.7273	Intermediate Similarity	NPC472853
0.7273	Intermediate Similarity	NPC125366
0.7273	Intermediate Similarity	NPC298266
0.7273	Intermediate Similarity	NPC134227
0.7273	Intermediate Similarity	NPC477172
0.7273	Intermediate Similarity	NPC259654
0.7264	Intermediate Similarity	NPC477465
0.7255	Intermediate Similarity	NPC293512
0.7255	Intermediate Similarity	NPC471430
0.7253	Intermediate Similarity	NPC62572
0.725	Intermediate Similarity	NPC19311
0.725	Intermediate Similarity	NPC230047
0.7245	Intermediate Similarity	NPC474724
0.7241	Intermediate Similarity	NPC177343
0.7241	Intermediate Similarity	NPC199965
0.7241	Intermediate Similarity	NPC476732
0.7241	Intermediate Similarity	NPC472608
0.7238	Intermediate Similarity	NPC157571
0.7228	Intermediate Similarity	NPC469827
0.7222	Intermediate Similarity	NPC111582
0.7222	Intermediate Similarity	NPC477285
0.7222	Intermediate Similarity	NPC227170
0.7216	Intermediate Similarity	NPC256227
0.7216	Intermediate Similarity	NPC237071
0.7216	Intermediate Similarity	NPC163685
0.7216	Intermediate Similarity	NPC238796
0.7216	Intermediate Similarity	NPC203434
0.7212	Intermediate Similarity	NPC471431
0.7212	Intermediate Similarity	NPC101450
0.7209	Intermediate Similarity	NPC4209
0.7209	Intermediate Similarity	NPC136424
0.7204	Intermediate Similarity	NPC236459
0.72	Intermediate Similarity	NPC470172
0.7191	Intermediate Similarity	NPC211049
0.7191	Intermediate Similarity	NPC45256
0.7191	Intermediate Similarity	NPC260977
0.7191	Intermediate Similarity	NPC30443
0.7191	Intermediate Similarity	NPC285480
0.7188	Intermediate Similarity	NPC151214
0.7188	Intermediate Similarity	NPC191915
0.7184	Intermediate Similarity	NPC469826

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 NPC79308 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	3293
0.2-0.3	3528
0.3-0.4	1130
0.4-0.5	425
0.5-0.6	230
0.6-0.7	137
0.7-0.8	8
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
0.7326	Intermediate Similarity	NPD6116	Phase 1
0.7209	Intermediate Similarity	NPD6117	Approved
0.7191	Intermediate Similarity	NPD1779	Approved
0.7191	Intermediate Similarity	NPD1780	Approved
0.7045	Intermediate Similarity	NPD6697	Approved
0.7045	Intermediate Similarity	NPD6118	Approved
0.7045	Intermediate Similarity	NPD6115	Approved
0.7045	Intermediate Similarity	NPD6114	Approved
0.7033	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3669	Approved
0.6977	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD1700	Approved
0.6897	Remote Similarity	NPD3702	Approved
0.6893	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD8133	Approved
0.6633	Remote Similarity	NPD8034	Phase 2
0.6633	Remote Similarity	NPD8035	Phase 2
0.6628	Remote Similarity	NPD4789	Approved
0.6627	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1810	Approved
0.6591	Remote Similarity	NPD1811	Approved
0.6552	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4224	Phase 2
0.6517	Remote Similarity	NPD3703	Phase 2
0.6512	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6675	Approved
0.6509	Remote Similarity	NPD6402	Approved
0.6509	Remote Similarity	NPD7128	Approved
0.6509	Remote Similarity	NPD5739	Approved
0.6481	Remote Similarity	NPD6373	Approved
0.6481	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6372	Approved
0.6466	Remote Similarity	NPD8328	Phase 3
0.6455	Remote Similarity	NPD8297	Approved
0.6455	Remote Similarity	NPD6882	Approved
0.6449	Remote Similarity	NPD5697	Approved
0.6449	Remote Similarity	NPD5701	Approved
0.6441	Remote Similarity	NPD8293	Discontinued
0.6429	Remote Similarity	NPD6940	Discontinued
0.6415	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4225	Approved
0.64	Remote Similarity	NPD8171	Discontinued
0.6395	Remote Similarity	NPD5360	Phase 3
0.6395	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD229	Approved
0.6389	Remote Similarity	NPD6686	Approved
0.6389	Remote Similarity	NPD6881	Approved
0.6389	Remote Similarity	NPD6899	Approved
0.6389	Remote Similarity	NPD7320	Approved
0.6387	Remote Similarity	NPD7736	Approved
0.6379	Remote Similarity	NPD6370	Approved
0.6364	Remote Similarity	NPD6650	Approved
0.6364	Remote Similarity	NPD6081	Approved
0.6364	Remote Similarity	NPD5777	Approved
0.6364	Remote Similarity	NPD6649	Approved
0.6354	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6012	Approved
0.633	Remote Similarity	NPD6013	Approved
0.633	Remote Similarity	NPD6014	Approved
0.6322	Remote Similarity	NPD3698	Phase 2
0.6311	Remote Similarity	NPD6084	Phase 2
0.6311	Remote Similarity	NPD6083	Phase 2
0.631	Remote Similarity	NPD371	Approved
0.6296	Remote Similarity	NPD6412	Phase 2
0.6273	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7102	Approved
0.6273	Remote Similarity	NPD7290	Approved
0.6273	Remote Similarity	NPD6883	Approved
0.6271	Remote Similarity	NPD7492	Approved
0.625	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD4244	Approved
0.625	Remote Similarity	NPD4245	Approved
0.6239	Remote Similarity	NPD6011	Approved
0.6238	Remote Similarity	NPD6399	Phase 3
0.6228	Remote Similarity	NPD6009	Approved
0.6218	Remote Similarity	NPD7507	Approved
0.6218	Remote Similarity	NPD6616	Approved
0.6216	Remote Similarity	NPD6869	Approved
0.6216	Remote Similarity	NPD6847	Approved
0.6216	Remote Similarity	NPD8130	Phase 1
0.6216	Remote Similarity	NPD6617	Approved
0.6207	Remote Similarity	NPD6054	Approved
0.6207	Remote Similarity	NPD6059	Approved
0.6207	Remote Similarity	NPD6319	Approved
0.618	Remote Similarity	NPD4758	Discontinued
0.6167	Remote Similarity	NPD7078	Approved
0.6154	Remote Similarity	NPD6016	Approved
0.6154	Remote Similarity	NPD6921	Approved
0.6154	Remote Similarity	NPD4755	Approved
0.6154	Remote Similarity	NPD7902	Approved
0.6154	Remote Similarity	NPD6015	Approved
0.6129	Remote Similarity	NPD3671	Phase 1
0.6117	Remote Similarity	NPD5695	Phase 3
0.6102	Remote Similarity	NPD5988	Approved
0.6087	Remote Similarity	NPD7115	Discovery
0.6071	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD2687	Approved
0.6067	Remote Similarity	NPD2254	Approved
0.6067	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD2686	Approved
0.6066	Remote Similarity	NPD7319	Approved
0.6047	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD4696	Approved
0.6038	Remote Similarity	NPD5285	Approved
0.6038	Remote Similarity	NPD5286	Approved
0.6038	Remote Similarity	NPD4700	Approved
0.6019	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6928	Phase 2
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD615	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7515	Phase 2
0.5978	Remote Similarity	NPD2257	Approved
0.596	Remote Similarity	NPD3618	Phase 1
0.5957	Remote Similarity	NPD5364	Discontinued
0.5941	Remote Similarity	NPD4753	Phase 2
0.5926	Remote Similarity	NPD5211	Phase 2
0.5926	Remote Similarity	NPD5226	Approved
0.5926	Remote Similarity	NPD5224	Approved
0.5926	Remote Similarity	NPD5225	Approved
0.5926	Remote Similarity	NPD4633	Approved
0.5905	Remote Similarity	NPD4697	Phase 3
0.5897	Remote Similarity	NPD7328	Approved
0.5897	Remote Similarity	NPD7327	Approved
0.5882	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5983	Phase 2
0.5872	Remote Similarity	NPD5175	Approved
0.5872	Remote Similarity	NPD5174	Approved
0.5865	Remote Similarity	NPD7900	Approved
0.5865	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD7516	Approved
0.5847	Remote Similarity	NPD7100	Approved
0.5847	Remote Similarity	NPD7101	Approved
0.5842	Remote Similarity	NPD5737	Approved
0.5842	Remote Similarity	NPD6672	Approved
0.5841	Remote Similarity	NPD4634	Approved
0.5833	Remote Similarity	NPD5223	Approved
0.5818	Remote Similarity	NPD5141	Approved
0.5812	Remote Similarity	NPD6317	Approved
0.581	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5210	Approved
0.581	Remote Similarity	NPD4629	Approved
0.5802	Remote Similarity	NPD3728	Approved
0.5802	Remote Similarity	NPD3730	Approved
0.5802	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD8377	Approved
0.5798	Remote Similarity	NPD8294	Approved
0.5794	Remote Similarity	NPD7638	Approved
0.5789	Remote Similarity	NPD4802	Phase 2
0.5789	Remote Similarity	NPD4238	Approved
0.5785	Remote Similarity	NPD7604	Phase 2
0.5785	Remote Similarity	NPD6067	Discontinued
0.578	Remote Similarity	NPD8084	Approved
0.578	Remote Similarity	NPD8139	Approved
0.578	Remote Similarity	NPD8138	Approved
0.578	Remote Similarity	NPD8086	Approved
0.578	Remote Similarity	NPD8085	Approved
0.578	Remote Similarity	NPD8083	Approved
0.578	Remote Similarity	NPD8082	Approved
0.5769	Remote Similarity	NPD4202	Approved
0.5766	Remote Similarity	NPD6008	Approved
0.5766	Remote Similarity	NPD4768	Approved
0.5766	Remote Similarity	NPD4767	Approved
0.5763	Remote Similarity	NPD6335	Approved
0.5763	Remote Similarity	NPD6314	Approved
0.5763	Remote Similarity	NPD6313	Approved
0.5755	Remote Similarity	NPD5222	Approved
0.5755	Remote Similarity	NPD5221	Approved
0.5755	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.575	Remote Similarity	NPD6908	Approved
0.575	Remote Similarity	NPD8378	Approved
0.575	Remote Similarity	NPD8380	Approved
0.575	Remote Similarity	NPD8517	Approved
0.575	Remote Similarity	NPD8335	Approved
0.575	Remote Similarity	NPD6909	Approved
0.575	Remote Similarity	NPD8516	Approved
0.575	Remote Similarity	NPD8379	Approved
0.575	Remote Similarity	NPD8515	Approved
0.575	Remote Similarity	NPD8033	Approved
0.575	Remote Similarity	NPD8513	Phase 3
0.575	Remote Similarity	NPD8296	Approved
0.5747	Remote Similarity	NPD7909	Approved
0.5741	Remote Similarity	NPD7639	Approved
0.5741	Remote Similarity	NPD7640	Approved
0.5741	Remote Similarity	NPD8418	Phase 2
0.573	Remote Similarity	NPD896	Approved
0.573	Remote Similarity	NPD898	Approved
0.573	Remote Similarity	NPD897	Approved
0.5727	Remote Similarity	NPD8275	Approved
0.5727	Remote Similarity	NPD4754	Approved
0.5727	Remote Similarity	NPD8276	Approved
0.5726	Remote Similarity	NPD6033	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