NPASS Compound

Structure

CID150755 OpenBabel06191715522D 25 26 0 0 1 0 0 0 0 0999 V2000 -3.5279 -2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7089 -4.1789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 -2.5772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0050 0.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2129 -0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2618 1.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 -1.8563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5493 -2.0255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0594 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1211 -3.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8061 -1.3563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2673 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 -1.7518 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1266 -3.4744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5003 -1.7164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1083 2.5962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7199 -4.3879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.6654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 13 1 0 0 0 0 7 15 1 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 10 21 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 9 1 6 0 0 0 15 17 1 0 0 0 0 15 24 1 6 0 0 0 16 8 1 1 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 17 12 1 6 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.16
Volume:	356.99
LogP:	1.307
LogD:	1.459
LogS:	-2.684
# Rotatable Bonds:	5
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.474
Synthetic Accessibility Score:	4.881
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.982
MDCK Permeability:	3.5903649404644966e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.067
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.612

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	75.31637573242188%
Volume Distribution (VD):	0.607
Pgp-substrate:	15.114374160766602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.424
CYP2C19-substrate:	0.145
CYP2C9-inhibitor:	0.677
CYP2C9-substrate:	0.202
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.675
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	5.994
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.232
Drug-inuced Liver Injury (DILI):	0.165
AMES Toxicity:	0.173
Rat Oral Acute Toxicity:	0.187
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.938
Carcinogencity:	0.79
Eye Corrosion:	0.251
Eye Irritation:	0.445
Respiratory Toxicity:	0.67

Download Data

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

Natural Product: NPC150755

Natural Product ID:	NPC150755
*Common Name:**	8Alpha-Methylacryloxy-14-Hydroxy-15-Al-3(4),11(13)-Germacradien-6,12-Olide
IUPAC Name:	[(3aR,4R,6R,9E,11aR)-10-formyl-6-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,6,7,8,11,11a-octahydrocyclodeca[b]furan-4-yl] 2-methylprop-2-enoate
Synonyms:
Standard InCHIKey:	ZAUICCJAIJSEIZ-MCBKFPHBSA-N
Standard InCHI:	InChI=1S/C19H24O6/c1-11(2)18(22)24-15-7-13(9-20)5-4-6-14(10-21)8-16-17(15)12(3)19(23)25-16/h6,10,13,15-17,20H,1,3-5,7-9H2,2H3/b14-6+/t13-,15-,16-,17-/m1/s1
SMILES:	OC[C@@H]1CC/C=C(/C=O)C[C@@H]2[C@@H]([C@@H](C1)OC(=O)C(=C)C)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL389476
PubChem CID:	44421659
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NA	Eurypon laughlini	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125227]
NA	Eurypon laughlini	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17291042]
NPO12604	Phakellia dendyi	Species	Bubaridae	Eukaryota	n.a.	Byron Strait, Papua New Guinea	2003	PMID[18327911]
NA	Eurypon laughlini	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19583251]
NA	Eurypon laughlini	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19743810]
NA	Eurypon laughlini	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24779644]
NA	Eurypon laughlini	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32484670]
NPO1540	Scopolia tangutica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6819	Cardopatium corymbosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3034	Lonchocarpus yucatanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7081	Sidastrum tehuacanum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3220	Aberia caffra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12604	Phakellia dendyi	Species	Bubaridae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		IC50	=	1500.0	nM	PMID[469171]

☑ 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 NPC150755 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	177
0.1-0.2	1122
0.2-0.3	4996
0.3-0.4	12394
0.4-0.5	11646
0.5-0.6	7163
0.6-0.7	3957
0.7-0.8	1030
0.8-0.85	123
0.85-0.9	63
0.9-0.95	20
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC475461
0.9512	High Similarity	NPC305475
0.939	High Similarity	NPC255307
0.9383	High Similarity	NPC59097
0.9268	High Similarity	NPC191476
0.9268	High Similarity	NPC114979
0.9146	High Similarity	NPC131669
0.9146	High Similarity	NPC473390
0.9146	High Similarity	NPC40746
0.9146	High Similarity	NPC169575
0.9036	High Similarity	NPC476804
0.9036	High Similarity	NPC96259
0.9036	High Similarity	NPC141193
0.9024	High Similarity	NPC229825
0.9012	High Similarity	NPC281132
0.8929	High Similarity	NPC470755
0.8902	High Similarity	NPC24417
0.8889	High Similarity	NPC167881
0.8889	High Similarity	NPC98557
0.8864	High Similarity	NPC125674
0.8864	High Similarity	NPC475838
0.8864	High Similarity	NPC228451
0.8851	High Similarity	NPC475855
0.8851	High Similarity	NPC469368
0.8837	High Similarity	NPC476805
0.881	High Similarity	NPC158756
0.8764	High Similarity	NPC474247
0.8706	High Similarity	NPC165162
0.8675	High Similarity	NPC52861
0.8659	High Similarity	NPC470244
0.8659	High Similarity	NPC270126
0.8659	High Similarity	NPC470239
0.8652	High Similarity	NPC475302
0.8642	High Similarity	NPC141789
0.8642	High Similarity	NPC171204
0.8642	High Similarity	NPC476028
0.8636	High Similarity	NPC179394
0.8636	High Similarity	NPC144133
0.8621	High Similarity	NPC476803
0.8621	High Similarity	NPC475819
0.8605	High Similarity	NPC469910
0.8571	High Similarity	NPC230800
0.8571	High Similarity	NPC89555
0.8571	High Similarity	NPC279621
0.8537	High Similarity	NPC108816
0.8537	High Similarity	NPC196653
0.8537	High Similarity	NPC93763
0.8537	High Similarity	NPC471465
0.8519	High Similarity	NPC235906
0.8471	Intermediate Similarity	NPC116543
0.8462	Intermediate Similarity	NPC477922
0.8462	Intermediate Similarity	NPC471141
0.8452	Intermediate Similarity	NPC301477
0.8452	Intermediate Similarity	NPC141810
0.8452	Intermediate Similarity	NPC25684
0.8452	Intermediate Similarity	NPC281949
0.8444	Intermediate Similarity	NPC162205
0.8444	Intermediate Similarity	NPC288240
0.8444	Intermediate Similarity	NPC273579
0.8444	Intermediate Similarity	NPC295204
0.8434	Intermediate Similarity	NPC617
0.8434	Intermediate Similarity	NPC89128
0.8427	Intermediate Similarity	NPC473619
0.8427	Intermediate Similarity	NPC129419
0.8415	Intermediate Similarity	NPC116177
0.8415	Intermediate Similarity	NPC476794
0.8415	Intermediate Similarity	NPC470240
0.8415	Intermediate Similarity	NPC7563
0.8415	Intermediate Similarity	NPC320630
0.8409	Intermediate Similarity	NPC202672
0.8409	Intermediate Similarity	NPC477302
0.8395	Intermediate Similarity	NPC155587
0.8391	Intermediate Similarity	NPC50637
0.8372	Intermediate Similarity	NPC115786
0.837	Intermediate Similarity	NPC477921
0.8333	Intermediate Similarity	NPC184463
0.8333	Intermediate Similarity	NPC473321
0.8315	Intermediate Similarity	NPC206001
0.8315	Intermediate Similarity	NPC295312
0.8315	Intermediate Similarity	NPC268298
0.8315	Intermediate Similarity	NPC474032
0.8315	Intermediate Similarity	NPC218927
0.8315	Intermediate Similarity	NPC166919
0.8298	Intermediate Similarity	NPC288876
0.8293	Intermediate Similarity	NPC68819
0.8276	Intermediate Similarity	NPC261380
0.8272	Intermediate Similarity	NPC476355
0.8261	Intermediate Similarity	NPC471142
0.8261	Intermediate Similarity	NPC304886
0.8256	Intermediate Similarity	NPC52609
0.8256	Intermediate Similarity	NPC474703
0.8256	Intermediate Similarity	NPC1761
0.8242	Intermediate Similarity	NPC469645
0.8242	Intermediate Similarity	NPC469692
0.8242	Intermediate Similarity	NPC475912
0.8242	Intermediate Similarity	NPC212486
0.8222	Intermediate Similarity	NPC474232
0.8214	Intermediate Similarity	NPC19841
0.8202	Intermediate Similarity	NPC136879
0.8202	Intermediate Similarity	NPC473715
0.8193	Intermediate Similarity	NPC97516
0.8191	Intermediate Similarity	NPC473326
0.8182	Intermediate Similarity	NPC261721
0.8182	Intermediate Similarity	NPC469483
0.8182	Intermediate Similarity	NPC107787
0.8172	Intermediate Similarity	NPC473859
0.8161	Intermediate Similarity	NPC82297
0.8161	Intermediate Similarity	NPC165287
0.8152	Intermediate Similarity	NPC57405
0.8152	Intermediate Similarity	NPC303942
0.8152	Intermediate Similarity	NPC121825
0.8152	Intermediate Similarity	NPC477131
0.8152	Intermediate Similarity	NPC474338
0.8148	Intermediate Similarity	NPC295633
0.8148	Intermediate Similarity	NPC269206
0.8148	Intermediate Similarity	NPC58956
0.8132	Intermediate Similarity	NPC12172
0.8132	Intermediate Similarity	NPC133698
0.8132	Intermediate Similarity	NPC208886
0.8132	Intermediate Similarity	NPC131209
0.8132	Intermediate Similarity	NPC30515
0.8111	Intermediate Similarity	NPC307411
0.8111	Intermediate Similarity	NPC151770
0.8095	Intermediate Similarity	NPC472960
0.8095	Intermediate Similarity	NPC267231
0.809	Intermediate Similarity	NPC160138
0.8085	Intermediate Similarity	NPC169205
0.8072	Intermediate Similarity	NPC123360
0.8068	Intermediate Similarity	NPC78089
0.8065	Intermediate Similarity	NPC193645
0.8065	Intermediate Similarity	NPC90121
0.8065	Intermediate Similarity	NPC48803
0.8065	Intermediate Similarity	NPC270013
0.8065	Intermediate Similarity	NPC14961
0.8065	Intermediate Similarity	NPC36954
0.8065	Intermediate Similarity	NPC475659
0.8065	Intermediate Similarity	NPC275960
0.8049	Intermediate Similarity	NPC140287
0.8046	Intermediate Similarity	NPC250315
0.8043	Intermediate Similarity	NPC476300
0.8043	Intermediate Similarity	NPC81419
0.8043	Intermediate Similarity	NPC179746
0.8025	Intermediate Similarity	NPC163003
0.8023	Intermediate Similarity	NPC470241
0.8023	Intermediate Similarity	NPC471325
0.8023	Intermediate Similarity	NPC325031
0.8022	Intermediate Similarity	NPC473448
0.8022	Intermediate Similarity	NPC51004
0.8021	Intermediate Similarity	NPC164598
0.8021	Intermediate Similarity	NPC474339
0.8021	Intermediate Similarity	NPC47880
0.8	Intermediate Similarity	NPC187268
0.8	Intermediate Similarity	NPC141191
0.8	Intermediate Similarity	NPC178277
0.8	Intermediate Similarity	NPC471144
0.7979	Intermediate Similarity	NPC185553
0.7979	Intermediate Similarity	NPC476315
0.7978	Intermediate Similarity	NPC284902
0.7976	Intermediate Similarity	NPC474760
0.7976	Intermediate Similarity	NPC187568
0.7976	Intermediate Similarity	NPC41780
0.7976	Intermediate Similarity	NPC65603
0.7957	Intermediate Similarity	NPC474035
0.7957	Intermediate Similarity	NPC140543
0.7957	Intermediate Similarity	NPC81386
0.7957	Intermediate Similarity	NPC473316
0.7957	Intermediate Similarity	NPC473330
0.7957	Intermediate Similarity	NPC198853
0.7955	Intermediate Similarity	NPC159635
0.7955	Intermediate Similarity	NPC156485
0.7952	Intermediate Similarity	NPC226669
0.7952	Intermediate Similarity	NPC138408
0.7952	Intermediate Similarity	NPC193351
0.7938	Intermediate Similarity	NPC471148
0.7938	Intermediate Similarity	NPC149371
0.7935	Intermediate Similarity	NPC261607
0.7935	Intermediate Similarity	NPC111114
0.7935	Intermediate Similarity	NPC300312
0.7935	Intermediate Similarity	NPC475925
0.7931	Intermediate Similarity	NPC474291
0.7931	Intermediate Similarity	NPC173609
0.7931	Intermediate Similarity	NPC85772
0.7907	Intermediate Similarity	NPC302426
0.7895	Intermediate Similarity	NPC161493
0.7889	Intermediate Similarity	NPC237540
0.7882	Intermediate Similarity	NPC128276
0.7872	Intermediate Similarity	NPC213698
0.7872	Intermediate Similarity	NPC67584
0.7872	Intermediate Similarity	NPC52044
0.7865	Intermediate Similarity	NPC21469
0.7865	Intermediate Similarity	NPC215364
0.7841	Intermediate Similarity	NPC272814
0.7841	Intermediate Similarity	NPC475947
0.7835	Intermediate Similarity	NPC150923
0.7835	Intermediate Similarity	NPC185141
0.7835	Intermediate Similarity	NPC476270
0.7835	Intermediate Similarity	NPC46998
0.7835	Intermediate Similarity	NPC110443
0.7835	Intermediate Similarity	NPC128733
0.7835	Intermediate Similarity	NPC133907

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 NPC150755 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1704
0.2-0.3	3751
0.3-0.4	2394
0.4-0.5	683
0.5-0.6	326
0.6-0.7	98
0.7-0.8	20
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
0.8065	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD46	Approved
0.7634	Intermediate Similarity	NPD6698	Approved
0.7447	Intermediate Similarity	NPD5785	Approved
0.7444	Intermediate Similarity	NPD7154	Phase 3
0.734	Intermediate Similarity	NPD1695	Approved
0.7283	Intermediate Similarity	NPD5363	Approved
0.7282	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4225	Approved
0.7263	Intermediate Similarity	NPD7838	Discovery
0.7143	Intermediate Similarity	NPD6435	Approved
0.7143	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1694	Approved
0.7075	Intermediate Similarity	NPD6371	Approved
0.7065	Intermediate Similarity	NPD5362	Discontinued
0.7033	Intermediate Similarity	NPD5369	Approved
0.6957	Remote Similarity	NPD4269	Approved
0.6957	Remote Similarity	NPD4270	Approved
0.6923	Remote Similarity	NPD4820	Approved
0.6923	Remote Similarity	NPD4821	Approved
0.6923	Remote Similarity	NPD4819	Approved
0.6923	Remote Similarity	NPD5368	Approved
0.6923	Remote Similarity	NPD4822	Approved
0.6889	Remote Similarity	NPD4268	Approved
0.6889	Remote Similarity	NPD4271	Approved
0.6887	Remote Similarity	NPD6686	Approved
0.6869	Remote Similarity	NPD5282	Discontinued
0.6842	Remote Similarity	NPD5786	Approved
0.6842	Remote Similarity	NPD4249	Approved
0.6837	Remote Similarity	NPD7983	Approved
0.6804	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6101	Approved
0.6771	Remote Similarity	NPD4250	Approved
0.6771	Remote Similarity	NPD4251	Approved
0.6768	Remote Similarity	NPD5779	Approved
0.6768	Remote Similarity	NPD6399	Phase 3
0.6768	Remote Similarity	NPD5778	Approved
0.6765	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4252	Approved
0.6703	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6411	Approved
0.6636	Remote Similarity	NPD6053	Discontinued
0.6632	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7638	Approved
0.6596	Remote Similarity	NPD5209	Approved
0.6549	Remote Similarity	NPD7115	Discovery
0.6538	Remote Similarity	NPD7640	Approved
0.6538	Remote Similarity	NPD7639	Approved
0.6526	Remote Similarity	NPD5332	Approved
0.6526	Remote Similarity	NPD5331	Approved
0.6505	Remote Similarity	NPD6084	Phase 2
0.6505	Remote Similarity	NPD6083	Phase 2
0.6505	Remote Similarity	NPD7902	Approved
0.6489	Remote Similarity	NPD4790	Discontinued
0.6481	Remote Similarity	NPD5697	Approved
0.6476	Remote Similarity	NPD5344	Discontinued
0.6471	Remote Similarity	NPD5695	Phase 3
0.6442	Remote Similarity	NPD5696	Approved
0.6422	Remote Similarity	NPD6881	Approved
0.6422	Remote Similarity	NPD6899	Approved
0.6413	Remote Similarity	NPD4756	Discovery
0.6408	Remote Similarity	NPD7839	Suspended
0.6396	Remote Similarity	NPD6650	Approved
0.6396	Remote Similarity	NPD6649	Approved
0.6389	Remote Similarity	NPD6402	Approved
0.6389	Remote Similarity	NPD5739	Approved
0.6389	Remote Similarity	NPD6675	Approved
0.6389	Remote Similarity	NPD7128	Approved
0.6374	Remote Similarity	NPD8039	Approved
0.6373	Remote Similarity	NPD7748	Approved
0.6364	Remote Similarity	NPD6014	Approved
0.6364	Remote Similarity	NPD6012	Approved
0.6364	Remote Similarity	NPD6373	Approved
0.6364	Remote Similarity	NPD6013	Approved
0.6364	Remote Similarity	NPD6372	Approved
0.6337	Remote Similarity	NPD7515	Phase 2
0.633	Remote Similarity	NPD5701	Approved
0.6327	Remote Similarity	NPD7521	Approved
0.6327	Remote Similarity	NPD5330	Approved
0.6327	Remote Similarity	NPD7334	Approved
0.6327	Remote Similarity	NPD7146	Approved
0.6327	Remote Similarity	NPD6409	Approved
0.6327	Remote Similarity	NPD3618	Phase 1
0.6327	Remote Similarity	NPD6684	Approved
0.6306	Remote Similarity	NPD7102	Approved
0.6306	Remote Similarity	NPD6883	Approved
0.6306	Remote Similarity	NPD7290	Approved
0.63	Remote Similarity	NPD5370	Suspended
0.6289	Remote Similarity	NPD3133	Approved
0.6289	Remote Similarity	NPD3665	Phase 1
0.6289	Remote Similarity	NPD3666	Approved
0.6273	Remote Similarity	NPD6011	Approved
0.6273	Remote Similarity	NPD7320	Approved
0.625	Remote Similarity	NPD4697	Phase 3
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD3667	Approved
0.6226	Remote Similarity	NPD6648	Approved
0.6216	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7900	Approved
0.6214	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4695	Discontinued
0.6207	Remote Similarity	NPD7641	Discontinued
0.6207	Remote Similarity	NPD7331	Phase 2
0.62	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5737	Approved
0.62	Remote Similarity	NPD6672	Approved
0.62	Remote Similarity	NPD6903	Approved
0.6195	Remote Similarity	NPD8297	Approved
0.6195	Remote Similarity	NPD6882	Approved
0.6176	Remote Similarity	NPD5284	Approved
0.6176	Remote Similarity	NPD5693	Phase 1
0.6176	Remote Similarity	NPD7637	Suspended
0.6176	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5281	Approved
0.6163	Remote Similarity	NPD3197	Phase 1
0.6162	Remote Similarity	NPD5279	Phase 3
0.6162	Remote Similarity	NPD6422	Discontinued
0.6161	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4629	Approved
0.6154	Remote Similarity	NPD5210	Approved
0.6139	Remote Similarity	NPD4753	Phase 2
0.6122	Remote Similarity	NPD4786	Approved
0.6116	Remote Similarity	NPD7507	Approved
0.6111	Remote Similarity	NPD5211	Phase 2
0.6092	Remote Similarity	NPD7341	Phase 2
0.6091	Remote Similarity	NPD6008	Approved
0.6083	Remote Similarity	NPD7642	Approved
0.6075	Remote Similarity	NPD5285	Approved
0.6075	Remote Similarity	NPD5286	Approved
0.6075	Remote Similarity	NPD4696	Approved
0.605	Remote Similarity	NPD8516	Approved
0.605	Remote Similarity	NPD8515	Approved
0.605	Remote Similarity	NPD8513	Phase 3
0.605	Remote Similarity	NPD8517	Approved
0.6047	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD4755	Approved
0.6036	Remote Similarity	NPD6412	Phase 2
0.6034	Remote Similarity	NPD6274	Approved
0.6023	Remote Similarity	NPD3704	Approved
0.6019	Remote Similarity	NPD8034	Phase 2
0.6019	Remote Similarity	NPD6079	Approved
0.6019	Remote Similarity	NPD8035	Phase 2
0.6	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5328	Approved
0.5968	Remote Similarity	NPD7319	Approved
0.5965	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5225	Approved
0.5963	Remote Similarity	NPD4633	Approved
0.5963	Remote Similarity	NPD5226	Approved
0.5963	Remote Similarity	NPD7632	Discontinued
0.5963	Remote Similarity	NPD5224	Approved
0.5962	Remote Similarity	NPD4202	Approved
0.596	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5222	Approved
0.5943	Remote Similarity	NPD5221	Approved
0.5943	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4700	Approved
0.5926	Remote Similarity	NPD3172	Approved
0.5922	Remote Similarity	NPD5207	Approved
0.5917	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6647	Phase 2
0.5909	Remote Similarity	NPD5174	Approved
0.5909	Remote Similarity	NPD5175	Approved
0.5893	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5173	Approved
0.5882	Remote Similarity	NPD7101	Approved
0.5882	Remote Similarity	NPD7100	Approved
0.5877	Remote Similarity	NPD2067	Discontinued
0.5876	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5223	Approved
0.5862	Remote Similarity	NPD4632	Approved
0.5859	Remote Similarity	NPD6695	Phase 3
0.5854	Remote Similarity	NPD4266	Approved
0.5854	Remote Similarity	NPD3194	Approved
0.5854	Remote Similarity	NPD8451	Approved
0.5854	Remote Similarity	NPD3195	Phase 2
0.5854	Remote Similarity	NPD3196	Approved
0.5847	Remote Similarity	NPD6317	Approved
0.5842	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6319	Approved
0.5833	Remote Similarity	NPD3732	Approved
0.5826	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6673	Approved
0.5825	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6904	Approved
0.5825	Remote Similarity	NPD6080	Approved
0.582	Remote Similarity	NPD7830	Approved
0.582	Remote Similarity	NPD7829	Approved
0.5814	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5781	Clinical (unspecified phase)

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