NPASS Compound

Structure

NPC278673 OpenBabel07101719252D 30 32 0 0 1 0 0 0 0 0999 V2000 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1836 0.8849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6449 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9757 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1449 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5516 -2.6160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 -1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 16 2 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 17 2 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 25 1 0 0 0 0 15 23 1 0 0 0 0 15 26 1 0 0 0 0 17 19 1 0 0 0 0 18 22 1 0 0 0 0 18 27 1 6 0 0 0 19 30 1 0 0 0 0 20 24 1 1 0 0 0 20 25 1 0 0 0 0 21 28 2 0 0 0 0 21 30 1 0 0 0 0 22 23 1 1 0 0 0 22 24 1 0 0 0 0 23 3 1 1 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.27
Volume:	448.692
LogP:	3.187
LogD:	3.28
LogS:	-4.141
# Rotatable Bonds:	5
TPSA:	94.06
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.59
Synthetic Accessibility Score:	5.333
Fsp3:	0.68
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.272
MDCK Permeability:	1.5267060007317923e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.303
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.239
Plasma Protein Binding (PPB):	95.79093170166016%
Volume Distribution (VD):	0.882
Pgp-substrate:	4.924677848815918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.391
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.705
CYP2C9-inhibitor:	0.146
CYP2C9-substrate:	0.225
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	8.082
Half-life (T1/2):	0.611

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.903
AMES Toxicity:	0.446
Rat Oral Acute Toxicity:	0.86
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.575
Carcinogencity:	0.717
Eye Corrosion:	0.008
Eye Irritation:	0.016
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC278673

Natural Product ID:	NPC278673
*Common Name:**	6Alpha,8Alpha,23-Trihydroxy-Labd-13(14),15,17-Trien-16,19-Olide
IUPAC Name:	(5Z)-5-[(E)-5-[(1R,2R,4S,4aR,5R,8aS)-2,4-dihydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enylidene]-4-methylfuran-2-one
Synonyms:
Standard InCHIKey:	UQABFAYKAMYBGT-AWYLHJDVSA-N
Standard InCHI:	InChI=1S/C25H38O5/c1-16(7-9-19-17(2)13-21(28)30-19)8-10-20-24(4)12-6-11-23(3,15-26)22(24)18(27)14-25(20,5)29/h7,9,13,18,20,22,26-27,29H,6,8,10-12,14-15H2,1-5H3/b16-7+,19-9-/t18-,20+,22-,23-,24+,25+/m0/s1
SMILES:	C/C(=CC=C/1C(=CC(=O)O1)C)/CC[C@@H]1[C@@]2(C)CCC[C@@](C)(CO)[C@@H]2[C@H](C[C@@]1(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524070
PubChem CID:	44157595
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33075	salvia dominica	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19459643]

☑ 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
Kd	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6478	Individual Protein	Tubulin--tyrosine ligase	Homo sapiens	Kd	=	110.0	nM	PMID[548802]

☑ 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 NPC278673 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	193
0.1-0.2	1166
0.2-0.3	3768
0.3-0.4	6436
0.4-0.5	14816
0.5-0.6	8299
0.6-0.7	6285
0.7-0.8	1547
0.8-0.85	127
0.85-0.9	51
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9457	High Similarity	NPC276110
0.9381	High Similarity	NPC34768
0.9286	High Similarity	NPC475074
0.9184	High Similarity	NPC471206
0.914	High Similarity	NPC105490
0.9091	High Similarity	NPC179380
0.9062	High Similarity	NPC38855
0.9032	High Similarity	NPC7349
0.898	High Similarity	NPC45897
0.8947	High Similarity	NPC16967
0.89	High Similarity	NPC302788
0.8878	High Similarity	NPC476081
0.8854	High Similarity	NPC51499
0.8817	High Similarity	NPC78973
0.8812	High Similarity	NPC50124
0.8791	High Similarity	NPC131813
0.8776	High Similarity	NPC11974
0.8763	High Similarity	NPC325229
0.8763	High Similarity	NPC275086
0.8737	High Similarity	NPC191521
0.8687	High Similarity	NPC11956
0.8687	High Similarity	NPC109195
0.8687	High Similarity	NPC475038
0.8673	High Similarity	NPC324841
0.8654	High Similarity	NPC44537
0.8641	High Similarity	NPC12795
0.8641	High Similarity	NPC177047
0.8632	High Similarity	NPC162615
0.8632	High Similarity	NPC152778
0.8632	High Similarity	NPC205034
0.8627	High Similarity	NPC137462
0.8627	High Similarity	NPC304276
0.8614	High Similarity	NPC81630
0.8602	High Similarity	NPC93411
0.8602	High Similarity	NPC106332
0.86	High Similarity	NPC97487
0.86	High Similarity	NPC23584
0.86	High Similarity	NPC189588
0.86	High Similarity	NPC10232
0.86	High Similarity	NPC187302
0.86	High Similarity	NPC120321
0.86	High Similarity	NPC120009
0.86	High Similarity	NPC196471
0.8586	High Similarity	NPC472554
0.8571	High Similarity	NPC171126
0.8542	High Similarity	NPC140277
0.8529	High Similarity	NPC471205
0.8529	High Similarity	NPC67321
0.8529	High Similarity	NPC187435
0.8511	High Similarity	NPC170633
0.85	High Similarity	NPC472552
0.8495	Intermediate Similarity	NPC166857
0.8485	Intermediate Similarity	NPC16601
0.8447	Intermediate Similarity	NPC38948
0.8438	Intermediate Similarity	NPC472641
0.8438	Intermediate Similarity	NPC110022
0.8438	Intermediate Similarity	NPC53555
0.8438	Intermediate Similarity	NPC472640
0.8431	Intermediate Similarity	NPC51719
0.8431	Intermediate Similarity	NPC220217
0.8431	Intermediate Similarity	NPC218158
0.8431	Intermediate Similarity	NPC119855
0.8421	Intermediate Similarity	NPC472642
0.8421	Intermediate Similarity	NPC310479
0.8421	Intermediate Similarity	NPC221111
0.8421	Intermediate Similarity	NPC280149
0.8416	Intermediate Similarity	NPC160583
0.8416	Intermediate Similarity	NPC471938
0.84	Intermediate Similarity	NPC222875
0.84	Intermediate Similarity	NPC25177
0.84	Intermediate Similarity	NPC295110
0.84	Intermediate Similarity	NPC268829
0.84	Intermediate Similarity	NPC471412
0.84	Intermediate Similarity	NPC247701
0.8367	Intermediate Similarity	NPC234993
0.8367	Intermediate Similarity	NPC475380
0.8367	Intermediate Similarity	NPC194132
0.8367	Intermediate Similarity	NPC165632
0.8367	Intermediate Similarity	NPC209297
0.8367	Intermediate Similarity	NPC260796
0.8367	Intermediate Similarity	NPC134072
0.8365	Intermediate Similarity	NPC206618
0.8365	Intermediate Similarity	NPC75389
0.8333	Intermediate Similarity	NPC329842
0.8333	Intermediate Similarity	NPC472822
0.8333	Intermediate Similarity	NPC471937
0.8317	Intermediate Similarity	NPC162973
0.8317	Intermediate Similarity	NPC471914
0.8317	Intermediate Similarity	NPC472815
0.8316	Intermediate Similarity	NPC16265
0.83	Intermediate Similarity	NPC471413
0.8286	Intermediate Similarity	NPC103491
0.8283	Intermediate Similarity	NPC311241
0.8283	Intermediate Similarity	NPC100912
0.8283	Intermediate Similarity	NPC475446
0.828	Intermediate Similarity	NPC474013
0.8269	Intermediate Similarity	NPC306265
0.8269	Intermediate Similarity	NPC275060
0.8265	Intermediate Similarity	NPC471915
0.8265	Intermediate Similarity	NPC472441
0.8265	Intermediate Similarity	NPC111273
0.8261	Intermediate Similarity	NPC311070
0.8261	Intermediate Similarity	NPC476927
0.8252	Intermediate Similarity	NPC295843
0.8252	Intermediate Similarity	NPC266570
0.8247	Intermediate Similarity	NPC472812
0.8247	Intermediate Similarity	NPC139692
0.8235	Intermediate Similarity	NPC472821
0.8235	Intermediate Similarity	NPC281378
0.8235	Intermediate Similarity	NPC171014
0.8229	Intermediate Similarity	NPC182136
0.8224	Intermediate Similarity	NPC154815
0.82	Intermediate Similarity	NPC107806
0.82	Intermediate Similarity	NPC474440
0.82	Intermediate Similarity	NPC72647
0.82	Intermediate Similarity	NPC218107
0.8191	Intermediate Similarity	NPC471219
0.819	Intermediate Similarity	NPC322912
0.819	Intermediate Similarity	NPC475030
0.8182	Intermediate Similarity	NPC213761
0.8182	Intermediate Similarity	NPC473153
0.8182	Intermediate Similarity	NPC35171
0.8173	Intermediate Similarity	NPC43063
0.8173	Intermediate Similarity	NPC122816
0.8173	Intermediate Similarity	NPC319438
0.8173	Intermediate Similarity	NPC109376
0.8173	Intermediate Similarity	NPC79298
0.8173	Intermediate Similarity	NPC216636
0.8172	Intermediate Similarity	NPC102048
0.8172	Intermediate Similarity	NPC32223
0.8163	Intermediate Similarity	NPC57117
0.8163	Intermediate Similarity	NPC161998
0.8163	Intermediate Similarity	NPC470255
0.8155	Intermediate Similarity	NPC200861
0.8152	Intermediate Similarity	NPC2524
0.8144	Intermediate Similarity	NPC72845
0.8144	Intermediate Similarity	NPC472811
0.8144	Intermediate Similarity	NPC78594
0.8137	Intermediate Similarity	NPC114540
0.8137	Intermediate Similarity	NPC32577
0.8137	Intermediate Similarity	NPC155332
0.8131	Intermediate Similarity	NPC247760
0.8125	Intermediate Similarity	NPC261320
0.8125	Intermediate Similarity	NPC314727
0.8119	Intermediate Similarity	NPC251680
0.8119	Intermediate Similarity	NPC47024
0.8113	Intermediate Similarity	NPC478209
0.8108	Intermediate Similarity	NPC257610
0.8108	Intermediate Similarity	NPC145074
0.8108	Intermediate Similarity	NPC114939
0.8108	Intermediate Similarity	NPC112936
0.8108	Intermediate Similarity	NPC41123
0.8105	Intermediate Similarity	NPC471796
0.81	Intermediate Similarity	NPC473244
0.81	Intermediate Similarity	NPC210337
0.81	Intermediate Similarity	NPC477719
0.81	Intermediate Similarity	NPC99726
0.81	Intermediate Similarity	NPC477718
0.8095	Intermediate Similarity	NPC224660
0.8095	Intermediate Similarity	NPC470024
0.8091	Intermediate Similarity	NPC16701
0.8077	Intermediate Similarity	NPC172867
0.8077	Intermediate Similarity	NPC478208
0.8077	Intermediate Similarity	NPC186668
0.8065	Intermediate Similarity	NPC42476
0.8058	Intermediate Similarity	NPC112009
0.8058	Intermediate Similarity	NPC474822
0.8058	Intermediate Similarity	NPC134270
0.8058	Intermediate Similarity	NPC473523
0.8043	Intermediate Similarity	NPC170303
0.8041	Intermediate Similarity	NPC220216
0.8041	Intermediate Similarity	NPC209816
0.8039	Intermediate Similarity	NPC475617
0.8037	Intermediate Similarity	NPC183603
0.8021	Intermediate Similarity	NPC472809
0.8021	Intermediate Similarity	NPC472810
0.8021	Intermediate Similarity	NPC291665
0.802	Intermediate Similarity	NPC181147
0.802	Intermediate Similarity	NPC108368
0.802	Intermediate Similarity	NPC57079
0.802	Intermediate Similarity	NPC92275
0.8018	Intermediate Similarity	NPC278681
0.8	Intermediate Similarity	NPC284194
0.8	Intermediate Similarity	NPC185287
0.8	Intermediate Similarity	NPC475781
0.8	Intermediate Similarity	NPC157380
0.8	Intermediate Similarity	NPC175145
0.8	Intermediate Similarity	NPC29952
0.8	Intermediate Similarity	NPC471765
0.8	Intermediate Similarity	NPC242848
0.8	Intermediate Similarity	NPC190713
0.8	Intermediate Similarity	NPC88009
0.8	Intermediate Similarity	NPC475069
0.8	Intermediate Similarity	NPC221801
0.8	Intermediate Similarity	NPC211810
0.7981	Intermediate Similarity	NPC473543
0.7981	Intermediate Similarity	NPC470321
0.7981	Intermediate Similarity	NPC201880
0.7981	Intermediate Similarity	NPC81567
0.7981	Intermediate Similarity	NPC473207

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 NPC278673 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1286
0.2-0.3	3545
0.3-0.4	2584
0.4-0.5	1074
0.5-0.6	261
0.6-0.7	200
0.7-0.8	35
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
0.82	Intermediate Similarity	NPD7638	Approved
0.8119	Intermediate Similarity	NPD7640	Approved
0.8119	Intermediate Similarity	NPD7639	Approved
0.7768	Intermediate Similarity	NPD7327	Approved
0.7768	Intermediate Similarity	NPD7328	Approved
0.7719	Intermediate Similarity	NPD7503	Approved
0.7699	Intermediate Similarity	NPD7516	Approved
0.7685	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD4225	Approved
0.7604	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6648	Approved
0.7565	Intermediate Similarity	NPD8380	Approved
0.7565	Intermediate Similarity	NPD8335	Approved
0.7565	Intermediate Similarity	NPD8379	Approved
0.7565	Intermediate Similarity	NPD8378	Approved
0.7565	Intermediate Similarity	NPD8296	Approved
0.7524	Intermediate Similarity	NPD5344	Discontinued
0.75	Intermediate Similarity	NPD6695	Phase 3
0.7478	Intermediate Similarity	NPD8294	Approved
0.7478	Intermediate Similarity	NPD8377	Approved
0.7455	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7632	Discontinued
0.7431	Intermediate Similarity	NPD6686	Approved
0.7426	Intermediate Similarity	NPD7637	Suspended
0.7414	Intermediate Similarity	NPD8033	Approved
0.7248	Intermediate Similarity	NPD7128	Approved
0.7248	Intermediate Similarity	NPD6675	Approved
0.7248	Intermediate Similarity	NPD6402	Approved
0.7248	Intermediate Similarity	NPD5739	Approved
0.7216	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7750	Discontinued
0.72	Intermediate Similarity	NPD7524	Approved
0.7188	Intermediate Similarity	NPD6931	Approved
0.7188	Intermediate Similarity	NPD6930	Phase 2
0.7188	Intermediate Similarity	NPD7525	Registered
0.7182	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7507	Approved
0.7131	Intermediate Similarity	NPD7319	Approved
0.7117	Intermediate Similarity	NPD7320	Approved
0.7117	Intermediate Similarity	NPD6899	Approved
0.7117	Intermediate Similarity	NPD6881	Approved
0.7115	Intermediate Similarity	NPD7748	Approved
0.7087	Intermediate Similarity	NPD7515	Phase 2
0.7083	Intermediate Similarity	NPD6929	Approved
0.7075	Intermediate Similarity	NPD7902	Approved
0.7071	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7115	Discovery
0.7059	Intermediate Similarity	NPD6051	Approved
0.7054	Intermediate Similarity	NPD6373	Approved
0.7054	Intermediate Similarity	NPD6372	Approved
0.7027	Intermediate Similarity	NPD5701	Approved
0.7027	Intermediate Similarity	NPD5697	Approved
0.7018	Intermediate Similarity	NPD6053	Discontinued
0.701	Intermediate Similarity	NPD7514	Phase 3
0.701	Intermediate Similarity	NPD7332	Phase 2
0.6991	Remote Similarity	NPD7102	Approved
0.6991	Remote Similarity	NPD6883	Approved
0.6991	Remote Similarity	NPD7290	Approved
0.699	Remote Similarity	NPD7838	Discovery
0.693	Remote Similarity	NPD8130	Phase 1
0.693	Remote Similarity	NPD6869	Approved
0.693	Remote Similarity	NPD6847	Approved
0.693	Remote Similarity	NPD6617	Approved
0.693	Remote Similarity	NPD6650	Approved
0.693	Remote Similarity	NPD6649	Approved
0.6923	Remote Similarity	NPD7087	Discontinued
0.6916	Remote Similarity	NPD6083	Phase 2
0.6916	Remote Similarity	NPD6084	Phase 2
0.6907	Remote Similarity	NPD7645	Phase 2
0.6903	Remote Similarity	NPD6012	Approved
0.6903	Remote Similarity	NPD6013	Approved
0.6903	Remote Similarity	NPD6014	Approved
0.6875	Remote Similarity	NPD6932	Approved
0.6875	Remote Similarity	NPD6925	Approved
0.6875	Remote Similarity	NPD5776	Phase 2
0.687	Remote Similarity	NPD6882	Approved
0.687	Remote Similarity	NPD8297	Approved
0.6857	Remote Similarity	NPD5778	Approved
0.6857	Remote Similarity	NPD5779	Approved
0.6857	Remote Similarity	NPD6399	Phase 3
0.6832	Remote Similarity	NPD6893	Approved
0.6814	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6011	Approved
0.6804	Remote Similarity	NPD7145	Approved
0.6792	Remote Similarity	NPD7900	Approved
0.6792	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6898	Phase 1
0.6768	Remote Similarity	NPD6902	Approved
0.6765	Remote Similarity	NPD3618	Phase 1
0.6759	Remote Similarity	NPD4755	Approved
0.6737	Remote Similarity	NPD6926	Approved
0.6737	Remote Similarity	NPD6924	Approved
0.6735	Remote Similarity	NPD6683	Phase 2
0.6731	Remote Similarity	NPD5328	Approved
0.6698	Remote Similarity	NPD4202	Approved
0.6697	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6637	Remote Similarity	NPD6008	Approved
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6636	Remote Similarity	NPD4700	Approved
0.6612	Remote Similarity	NPD6319	Approved
0.6604	Remote Similarity	NPD6411	Approved
0.6604	Remote Similarity	NPD8035	Phase 2
0.6604	Remote Similarity	NPD8034	Phase 2
0.6604	Remote Similarity	NPD6079	Approved
0.6602	Remote Similarity	NPD7334	Approved
0.6602	Remote Similarity	NPD6684	Approved
0.6602	Remote Similarity	NPD6409	Approved
0.6602	Remote Similarity	NPD5330	Approved
0.6602	Remote Similarity	NPD7521	Approved
0.6602	Remote Similarity	NPD7146	Approved
0.6598	Remote Similarity	NPD6933	Approved
0.6579	Remote Similarity	NPD6412	Phase 2
0.6574	Remote Similarity	NPD5695	Phase 3
0.6555	Remote Similarity	NPD6274	Approved
0.6549	Remote Similarity	NPD5141	Approved
0.6545	Remote Similarity	NPD5696	Approved
0.6538	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7492	Approved
0.6529	Remote Similarity	NPD7101	Approved
0.6529	Remote Similarity	NPD7100	Approved
0.6525	Remote Similarity	NPD8133	Approved
0.6518	Remote Similarity	NPD5226	Approved
0.6518	Remote Similarity	NPD5224	Approved
0.6518	Remote Similarity	NPD5225	Approved
0.6518	Remote Similarity	NPD4633	Approved
0.6505	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6009	Approved
0.6495	Remote Similarity	NPD8264	Approved
0.6495	Remote Similarity	NPD7339	Approved
0.6495	Remote Similarity	NPD6942	Approved
0.648	Remote Similarity	NPD6616	Approved
0.6476	Remote Similarity	NPD6672	Approved
0.6476	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5737	Approved
0.6476	Remote Similarity	NPD6903	Approved
0.6475	Remote Similarity	NPD6059	Approved
0.6475	Remote Similarity	NPD6054	Approved
0.6465	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5175	Approved
0.646	Remote Similarity	NPD5174	Approved
0.6452	Remote Similarity	NPD7604	Phase 2
0.6449	Remote Similarity	NPD5693	Phase 1
0.6449	Remote Similarity	NPD5284	Approved
0.6449	Remote Similarity	NPD5281	Approved
0.6446	Remote Similarity	NPD6335	Approved
0.6429	Remote Similarity	NPD7078	Approved
0.6429	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4159	Approved
0.6429	Remote Similarity	NPD5223	Approved
0.6429	Remote Similarity	NPD8293	Discontinued
0.6423	Remote Similarity	NPD6908	Approved
0.6423	Remote Similarity	NPD5983	Phase 2
0.6423	Remote Similarity	NPD6909	Approved
0.6422	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6101	Approved
0.6415	Remote Similarity	NPD4753	Phase 2
0.641	Remote Similarity	NPD6371	Approved
0.641	Remote Similarity	NPD4634	Approved
0.6408	Remote Similarity	NPD3666	Approved
0.6408	Remote Similarity	NPD4786	Approved
0.6408	Remote Similarity	NPD3133	Approved
0.6408	Remote Similarity	NPD3665	Phase 1
0.6381	Remote Similarity	NPD4251	Approved
0.6381	Remote Similarity	NPD4250	Approved
0.6381	Remote Similarity	NPD3573	Approved
0.6378	Remote Similarity	NPD7736	Approved
0.6373	Remote Similarity	NPD3667	Approved
0.6371	Remote Similarity	NPD6370	Approved
0.6364	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5221	Approved
0.6364	Remote Similarity	NPD5222	Approved
0.6364	Remote Similarity	NPD4697	Phase 3
0.6364	Remote Similarity	NPD6317	Approved
0.6354	Remote Similarity	NPD7150	Approved
0.6354	Remote Similarity	NPD7152	Approved
0.6354	Remote Similarity	NPD7151	Approved
0.6349	Remote Similarity	NPD6336	Discontinued
0.6348	Remote Similarity	NPD6640	Phase 3
0.6348	Remote Similarity	NPD4767	Approved
0.6348	Remote Similarity	NPD4768	Approved
0.6346	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5282	Discontinued
0.6325	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.632	Remote Similarity	NPD8328	Phase 3
0.6316	Remote Similarity	NPD6922	Approved
0.6316	Remote Similarity	NPD6923	Approved
0.6316	Remote Similarity	NPD4754	Approved
0.6311	Remote Similarity	NPD7154	Phase 3
0.6311	Remote Similarity	NPD6313	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