NPASS Compound

Structure

NPC34768 OpenBabel07101718312D 31 33 0 0 1 0 0 0 0 0999 V2000 5.0433 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6535 0.8589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5217 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0070 -2.2964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8839 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2028 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7244 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3622 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1011 -0.8118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 -1.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4517 -0.0905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 -1.4559 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5650 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5217 -0.4853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6158 -1.6524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 -0.4853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9706 -1.6811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 0.0000 0.0000 C 0 0 1 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 2.5217 -1.4559 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0106 -2.5390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9412 -1.6811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4853 -2.5217 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4923 -1.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6664 -1.4506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 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 15 2 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 18 2 0 0 0 0 10 19 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 0 0 0 0 16 18 1 0 0 0 0 17 21 1 0 0 0 0 17 26 1 6 0 0 0 18 31 1 0 0 0 0 19 23 1 1 0 0 0 19 25 1 0 0 0 0 20 27 2 0 0 0 0 20 31 1 0 0 0 0 21 23 1 1 0 0 0 21 24 1 0 0 0 0 22 24 1 0 0 0 0 22 28 2 0 0 0 0 22 29 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 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.25
Volume:	454.846
LogP:	3.125
LogD:	2.609
LogS:	-3.699
# Rotatable Bonds:	5
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	5.246
Fsp3:	0.64
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:	-5.58
MDCK Permeability:	1.0988270332745742e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	0.116

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.121
Plasma Protein Binding (PPB):	95.66765594482422%
Volume Distribution (VD):	0.444
Pgp-substrate:	7.930178165435791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.51
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.3
CYP2C9-inhibitor:	0.106
CYP2C9-substrate:	0.245
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.261
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	2.243
Half-life (T1/2):	0.676

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.958
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.248
Rat Oral Acute Toxicity:	0.713
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.57
Carcinogencity:	0.784
Eye Corrosion:	0.009
Eye Irritation:	0.015
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC34768

Natural Product ID:	NPC34768
*Common Name:**	6Alpha,8Alpha-Dihydroxy-23-Carbossi-Labd-13(14),15,17-Trien-16,19-Olide
IUPAC Name:	(1R,4aS,5R,6R,8S,8aR)-6,8-dihydroxy-1,4a,6-trimethyl-5-[(E,5Z)-3-methyl-5-(3-methyl-5-oxofuran-2-ylidene)pent-3-enyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	ZZIIUCYVTHXMHB-HXHNTWCGSA-N
Standard InCHI:	InChI=1S/C25H36O6/c1-15(7-9-18-16(2)13-20(27)31-18)8-10-19-23(3)11-6-12-24(4,22(28)29)21(23)17(26)14-25(19,5)30/h7,9,13,17,19,21,26,30H,6,8,10-12,14H2,1-5H3,(H,28,29)/b15-7+,18-9-/t17-,19+,21+,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)([C@@H]2[C@H](C[C@@]1(C)O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496193
PubChem CID:	44157612
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	=	93.0	nM	PMID[492101]

☑ 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 NPC34768 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	202
0.1-0.2	1094
0.2-0.3	3433
0.3-0.4	6022
0.4-0.5	12944
0.5-0.6	9237
0.6-0.7	6974
0.7-0.8	2588
0.8-0.85	168
0.85-0.9	24
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC179380
0.95	High Similarity	NPC302788
0.949	High Similarity	NPC476081
0.9381	High Similarity	NPC278673
0.92	High Similarity	NPC120321
0.9118	High Similarity	NPC187435
0.9118	High Similarity	NPC67321
0.8878	High Similarity	NPC276110
0.8846	High Similarity	NPC306265
0.8812	High Similarity	NPC471412
0.8788	High Similarity	NPC234993
0.8788	High Similarity	NPC134072
0.875	High Similarity	NPC475074
0.8725	High Similarity	NPC162973
0.8713	High Similarity	NPC471413
0.8713	High Similarity	NPC47024
0.8679	High Similarity	NPC478209
0.8673	High Similarity	NPC139692
0.8654	High Similarity	NPC266570
0.8654	High Similarity	NPC471206
0.8654	High Similarity	NPC478208
0.86	High Similarity	NPC16967
0.8586	High Similarity	NPC105490
0.8544	High Similarity	NPC469606
0.8544	High Similarity	NPC273005
0.8544	High Similarity	NPC155332
0.8544	High Similarity	NPC32577
0.8544	High Similarity	NPC165250
0.8544	High Similarity	NPC31058
0.8544	High Similarity	NPC114540
0.8529	High Similarity	NPC38855
0.8485	Intermediate Similarity	NPC7349
0.8482	Intermediate Similarity	NPC41123
0.8482	Intermediate Similarity	NPC145074
0.8482	Intermediate Similarity	NPC114939
0.8476	Intermediate Similarity	NPC469607
0.8476	Intermediate Similarity	NPC478052
0.8468	Intermediate Similarity	NPC146786
0.8462	Intermediate Similarity	NPC45897
0.8462	Intermediate Similarity	NPC112009
0.844	Intermediate Similarity	NPC474271
0.844	Intermediate Similarity	NPC478212
0.8431	Intermediate Similarity	NPC216478
0.8431	Intermediate Similarity	NPC57079
0.8431	Intermediate Similarity	NPC108368
0.8416	Intermediate Similarity	NPC29952
0.8416	Intermediate Similarity	NPC242848
0.8411	Intermediate Similarity	NPC137911
0.8411	Intermediate Similarity	NPC228477
0.8411	Intermediate Similarity	NPC478210
0.84	Intermediate Similarity	NPC191521
0.8367	Intermediate Similarity	NPC174342
0.8365	Intermediate Similarity	NPC109195
0.8365	Intermediate Similarity	NPC475038
0.835	Intermediate Similarity	NPC54705
0.8333	Intermediate Similarity	NPC175351
0.8333	Intermediate Similarity	NPC478211
0.8333	Intermediate Similarity	NPC51499
0.8333	Intermediate Similarity	NPC132753
0.8333	Intermediate Similarity	NPC151681
0.8333	Intermediate Similarity	NPC473963
0.8333	Intermediate Similarity	NPC121402
0.8333	Intermediate Similarity	NPC224356
0.8318	Intermediate Similarity	NPC50124
0.8318	Intermediate Similarity	NPC275539
0.8318	Intermediate Similarity	NPC189075
0.8317	Intermediate Similarity	NPC259042
0.8317	Intermediate Similarity	NPC157686
0.8302	Intermediate Similarity	NPC81630
0.83	Intermediate Similarity	NPC205034
0.83	Intermediate Similarity	NPC162615
0.83	Intermediate Similarity	NPC152778
0.8288	Intermediate Similarity	NPC471816
0.8286	Intermediate Similarity	NPC471208
0.8286	Intermediate Similarity	NPC180204
0.8286	Intermediate Similarity	NPC329345
0.8286	Intermediate Similarity	NPC23584
0.8286	Intermediate Similarity	NPC473283
0.8286	Intermediate Similarity	NPC478057
0.8286	Intermediate Similarity	NPC475526
0.8283	Intermediate Similarity	NPC78973
0.8273	Intermediate Similarity	NPC471204
0.8269	Intermediate Similarity	NPC115899
0.8269	Intermediate Similarity	NPC303559
0.8269	Intermediate Similarity	NPC11974
0.8257	Intermediate Similarity	NPC132790
0.8257	Intermediate Similarity	NPC469655
0.8257	Intermediate Similarity	NPC247031
0.8257	Intermediate Similarity	NPC100329
0.8257	Intermediate Similarity	NPC474846
0.8257	Intermediate Similarity	NPC469656
0.8257	Intermediate Similarity	NPC97939
0.8252	Intermediate Similarity	NPC325229
0.8252	Intermediate Similarity	NPC275086
0.8247	Intermediate Similarity	NPC131813
0.8241	Intermediate Similarity	NPC475065
0.8241	Intermediate Similarity	NPC284828
0.8241	Intermediate Similarity	NPC5475
0.8241	Intermediate Similarity	NPC173905
0.8241	Intermediate Similarity	NPC472216
0.8235	Intermediate Similarity	NPC93245
0.8235	Intermediate Similarity	NPC154526
0.8235	Intermediate Similarity	NPC472362
0.8235	Intermediate Similarity	NPC473964
0.8235	Intermediate Similarity	NPC202833
0.8235	Intermediate Similarity	NPC472363
0.8224	Intermediate Similarity	NPC329048
0.8224	Intermediate Similarity	NPC330011
0.8224	Intermediate Similarity	NPC110496
0.8224	Intermediate Similarity	NPC143609
0.8218	Intermediate Similarity	NPC57117
0.8218	Intermediate Similarity	NPC24861
0.8218	Intermediate Similarity	NPC225474
0.8218	Intermediate Similarity	NPC469596
0.8218	Intermediate Similarity	NPC148000
0.8214	Intermediate Similarity	NPC478204
0.8205	Intermediate Similarity	NPC476008
0.82	Intermediate Similarity	NPC72845
0.819	Intermediate Similarity	NPC11956
0.819	Intermediate Similarity	NPC472552
0.8182	Intermediate Similarity	NPC44537
0.8182	Intermediate Similarity	NPC470063
0.8173	Intermediate Similarity	NPC266955
0.8173	Intermediate Similarity	NPC474012
0.8173	Intermediate Similarity	NPC476767
0.8173	Intermediate Similarity	NPC201406
0.8173	Intermediate Similarity	NPC476299
0.8173	Intermediate Similarity	NPC16601
0.8173	Intermediate Similarity	NPC117685
0.8173	Intermediate Similarity	NPC251680
0.8173	Intermediate Similarity	NPC324841
0.8173	Intermediate Similarity	NPC470074
0.8165	Intermediate Similarity	NPC12795
0.8165	Intermediate Similarity	NPC16270
0.8165	Intermediate Similarity	NPC177047
0.8165	Intermediate Similarity	NPC472666
0.8158	Intermediate Similarity	NPC184555
0.8155	Intermediate Similarity	NPC53844
0.8155	Intermediate Similarity	NPC91695
0.8155	Intermediate Similarity	NPC110937
0.8155	Intermediate Similarity	NPC100912
0.8155	Intermediate Similarity	NPC136781
0.8155	Intermediate Similarity	NPC70145
0.8148	Intermediate Similarity	NPC325054
0.8148	Intermediate Similarity	NPC475418
0.8148	Intermediate Similarity	NPC318363
0.8148	Intermediate Similarity	NPC476479
0.8148	Intermediate Similarity	NPC473482
0.8148	Intermediate Similarity	NPC137462
0.8148	Intermediate Similarity	NPC102843
0.8148	Intermediate Similarity	NPC304276
0.8142	Intermediate Similarity	NPC478205
0.8142	Intermediate Similarity	NPC478206
0.8142	Intermediate Similarity	NPC108581
0.8137	Intermediate Similarity	NPC183012
0.8137	Intermediate Similarity	NPC266899
0.8131	Intermediate Similarity	NPC252296
0.8131	Intermediate Similarity	NPC477125
0.8131	Intermediate Similarity	NPC189863
0.8131	Intermediate Similarity	NPC111952
0.8131	Intermediate Similarity	NPC218158
0.8125	Intermediate Similarity	NPC469794
0.8125	Intermediate Similarity	NPC72772
0.812	Intermediate Similarity	NPC477745
0.8119	Intermediate Similarity	NPC472640
0.8119	Intermediate Similarity	NPC110022
0.8119	Intermediate Similarity	NPC472641
0.8113	Intermediate Similarity	NPC159533
0.8113	Intermediate Similarity	NPC120009
0.8113	Intermediate Similarity	NPC36688
0.8113	Intermediate Similarity	NPC187302
0.8113	Intermediate Similarity	NPC196471
0.8113	Intermediate Similarity	NPC471938
0.8113	Intermediate Similarity	NPC476848
0.8113	Intermediate Similarity	NPC189588
0.8113	Intermediate Similarity	NPC72151
0.8113	Intermediate Similarity	NPC291154
0.8113	Intermediate Similarity	NPC97487
0.8113	Intermediate Similarity	NPC10232
0.8108	Intermediate Similarity	NPC469463
0.8108	Intermediate Similarity	NPC475966
0.8108	Intermediate Similarity	NPC469454
0.8108	Intermediate Similarity	NPC171126
0.8108	Intermediate Similarity	NPC469496
0.8108	Intermediate Similarity	NPC25909
0.8103	Intermediate Similarity	NPC55602
0.81	Intermediate Similarity	NPC280149
0.81	Intermediate Similarity	NPC310479
0.81	Intermediate Similarity	NPC232202
0.81	Intermediate Similarity	NPC472642
0.81	Intermediate Similarity	NPC221111
0.8095	Intermediate Similarity	NPC282524
0.8095	Intermediate Similarity	NPC235142
0.8095	Intermediate Similarity	NPC168319
0.8095	Intermediate Similarity	NPC194028
0.8095	Intermediate Similarity	NPC472554
0.8081	Intermediate Similarity	NPC104560
0.8081	Intermediate Similarity	NPC472302
0.8081	Intermediate Similarity	NPC93411
0.8081	Intermediate Similarity	NPC106332

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 NPC34768 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1287
0.2-0.3	3279
0.3-0.4	2641
0.4-0.5	1175
0.5-0.6	317
0.6-0.7	213
0.7-0.8	61
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
0.8252	Intermediate Similarity	NPD7638	Approved
0.8173	Intermediate Similarity	NPD7640	Approved
0.8173	Intermediate Similarity	NPD7639	Approved
0.8073	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6686	Approved
0.7736	Intermediate Similarity	NPD4225	Approved
0.7727	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7902	Approved
0.7636	Intermediate Similarity	NPD6402	Approved
0.7636	Intermediate Similarity	NPD5739	Approved
0.7636	Intermediate Similarity	NPD7128	Approved
0.7636	Intermediate Similarity	NPD6675	Approved
0.7589	Intermediate Similarity	NPD6372	Approved
0.7589	Intermediate Similarity	NPD6373	Approved
0.7586	Intermediate Similarity	NPD7115	Discovery
0.7524	Intermediate Similarity	NPD7748	Approved
0.7523	Intermediate Similarity	NPD7632	Discontinued
0.7521	Intermediate Similarity	NPD7507	Approved
0.75	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.748	Intermediate Similarity	NPD7319	Approved
0.7456	Intermediate Similarity	NPD6650	Approved
0.7456	Intermediate Similarity	NPD6649	Approved
0.7429	Intermediate Similarity	NPD6399	Phase 3
0.7411	Intermediate Similarity	NPD5701	Approved
0.7411	Intermediate Similarity	NPD5697	Approved
0.7391	Intermediate Similarity	NPD6053	Discontinued
0.7373	Intermediate Similarity	NPD7328	Approved
0.7373	Intermediate Similarity	NPD7327	Approved
0.7368	Intermediate Similarity	NPD7102	Approved
0.7368	Intermediate Similarity	NPD7290	Approved
0.7368	Intermediate Similarity	NPD6883	Approved
0.7358	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7900	Approved
0.7353	Intermediate Similarity	NPD3618	Phase 1
0.7345	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7503	Approved
0.7333	Intermediate Similarity	NPD7637	Suspended
0.7315	Intermediate Similarity	NPD6083	Phase 2
0.7315	Intermediate Similarity	NPD6084	Phase 2
0.7311	Intermediate Similarity	NPD7516	Approved
0.7304	Intermediate Similarity	NPD6869	Approved
0.7304	Intermediate Similarity	NPD6847	Approved
0.7304	Intermediate Similarity	NPD8130	Phase 1
0.7304	Intermediate Similarity	NPD6617	Approved
0.7281	Intermediate Similarity	NPD6014	Approved
0.7281	Intermediate Similarity	NPD6012	Approved
0.7281	Intermediate Similarity	NPD6013	Approved
0.7264	Intermediate Similarity	NPD5778	Approved
0.7264	Intermediate Similarity	NPD5779	Approved
0.7255	Intermediate Similarity	NPD1694	Approved
0.7241	Intermediate Similarity	NPD8297	Approved
0.7241	Intermediate Similarity	NPD6882	Approved
0.7193	Intermediate Similarity	NPD6011	Approved
0.719	Intermediate Similarity	NPD8380	Approved
0.719	Intermediate Similarity	NPD8379	Approved
0.719	Intermediate Similarity	NPD8335	Approved
0.719	Intermediate Similarity	NPD8378	Approved
0.719	Intermediate Similarity	NPD8296	Approved
0.7182	Intermediate Similarity	NPD6648	Approved
0.717	Intermediate Similarity	NPD8034	Phase 2
0.717	Intermediate Similarity	NPD8035	Phase 2
0.7168	Intermediate Similarity	NPD6008	Approved
0.7157	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD4755	Approved
0.7155	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5328	Approved
0.7117	Intermediate Similarity	NPD5344	Discontinued
0.7107	Intermediate Similarity	NPD8377	Approved
0.7107	Intermediate Similarity	NPD8294	Approved
0.7103	Intermediate Similarity	NPD4202	Approved
0.7091	Intermediate Similarity	NPD5696	Approved
0.7075	Intermediate Similarity	NPD46	Approved
0.7075	Intermediate Similarity	NPD6698	Approved
0.7059	Intermediate Similarity	NPD6695	Phase 3
0.7054	Intermediate Similarity	NPD5211	Phase 2
0.7049	Intermediate Similarity	NPD8033	Approved
0.7034	Intermediate Similarity	NPD4632	Approved
0.7027	Intermediate Similarity	NPD5285	Approved
0.7027	Intermediate Similarity	NPD4700	Approved
0.7027	Intermediate Similarity	NPD5286	Approved
0.7027	Intermediate Similarity	NPD4696	Approved
0.7019	Intermediate Similarity	NPD7521	Approved
0.7019	Intermediate Similarity	NPD7334	Approved
0.7019	Intermediate Similarity	NPD6409	Approved
0.7019	Intermediate Similarity	NPD6684	Approved
0.7019	Intermediate Similarity	NPD5330	Approved
0.7019	Intermediate Similarity	NPD7146	Approved
0.7009	Intermediate Similarity	NPD5284	Approved
0.7009	Intermediate Similarity	NPD6411	Approved
0.7009	Intermediate Similarity	NPD5281	Approved
0.7009	Intermediate Similarity	NPD6079	Approved
0.6972	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5695	Phase 3
0.6967	Remote Similarity	NPD6319	Approved
0.6957	Remote Similarity	NPD6412	Phase 2
0.693	Remote Similarity	NPD5141	Approved
0.6923	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6371	Approved
0.6917	Remote Similarity	NPD6274	Approved
0.6909	Remote Similarity	NPD4697	Phase 3
0.6903	Remote Similarity	NPD5225	Approved
0.6903	Remote Similarity	NPD4633	Approved
0.6903	Remote Similarity	NPD5224	Approved
0.6903	Remote Similarity	NPD5226	Approved
0.6891	Remote Similarity	NPD8133	Approved
0.6887	Remote Similarity	NPD5737	Approved
0.6887	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6672	Approved
0.6887	Remote Similarity	NPD6903	Approved
0.6885	Remote Similarity	NPD7101	Approved
0.6885	Remote Similarity	NPD7100	Approved
0.6881	Remote Similarity	NPD5282	Discontinued
0.688	Remote Similarity	NPD7492	Approved
0.686	Remote Similarity	NPD6009	Approved
0.6852	Remote Similarity	NPD5693	Phase 1
0.6842	Remote Similarity	NPD5174	Approved
0.6842	Remote Similarity	NPD5175	Approved
0.6838	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6059	Approved
0.6829	Remote Similarity	NPD6054	Approved
0.6827	Remote Similarity	NPD4786	Approved
0.6827	Remote Similarity	NPD3666	Approved
0.6827	Remote Similarity	NPD3665	Phase 1
0.6827	Remote Similarity	NPD3133	Approved
0.6825	Remote Similarity	NPD6616	Approved
0.6822	Remote Similarity	NPD6101	Approved
0.6822	Remote Similarity	NPD4753	Phase 2
0.6822	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5223	Approved
0.6803	Remote Similarity	NPD6335	Approved
0.68	Remote Similarity	NPD7604	Phase 2
0.68	Remote Similarity	NPD8328	Phase 3
0.6796	Remote Similarity	NPD3667	Approved
0.6792	Remote Similarity	NPD7750	Discontinued
0.6792	Remote Similarity	NPD3573	Approved
0.6792	Remote Similarity	NPD7524	Approved
0.6786	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4634	Approved
0.6774	Remote Similarity	NPD6908	Approved
0.6774	Remote Similarity	NPD5983	Phase 2
0.6774	Remote Similarity	NPD8513	Phase 3
0.6774	Remote Similarity	NPD6909	Approved
0.6774	Remote Similarity	NPD8516	Approved
0.6774	Remote Similarity	NPD8517	Approved
0.6774	Remote Similarity	NPD8515	Approved
0.6772	Remote Similarity	NPD7078	Approved
0.6772	Remote Similarity	NPD8293	Discontinued
0.6765	Remote Similarity	NPD6931	Approved
0.6765	Remote Similarity	NPD7525	Registered
0.6765	Remote Similarity	NPD6930	Phase 2
0.6759	Remote Similarity	NPD7838	Discovery
0.6759	Remote Similarity	NPD5785	Approved
0.6757	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5222	Approved
0.6757	Remote Similarity	NPD5221	Approved
0.6731	Remote Similarity	NPD7154	Phase 3
0.6724	Remote Similarity	NPD4767	Approved
0.6724	Remote Similarity	NPD4768	Approved
0.6721	Remote Similarity	NPD6317	Approved
0.672	Remote Similarity	NPD6370	Approved
0.6719	Remote Similarity	NPD7736	Approved
0.6698	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5279	Phase 3
0.6697	Remote Similarity	NPD6050	Approved
0.6696	Remote Similarity	NPD4754	Approved
0.6696	Remote Similarity	NPD5173	Approved
0.6693	Remote Similarity	NPD6336	Discontinued
0.6692	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6929	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.664	Remote Similarity	NPD6921	Approved
0.664	Remote Similarity	NPD6016	Approved
0.664	Remote Similarity	NPD6015	Approved
0.664	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6868	Approved
0.661	Remote Similarity	NPD5128	Approved
0.661	Remote Similarity	NPD4730	Approved
0.661	Remote Similarity	NPD4729	Approved
0.6606	Remote Similarity	NPD5692	Phase 3
0.6606	Remote Similarity	NPD5207	Approved
0.6602	Remote Similarity	NPD7332	Phase 2
0.6602	Remote Similarity	NPD7514	Phase 3
0.66	Remote Similarity	NPD8039	Approved
0.6587	Remote Similarity	NPD5988	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