NPASS Compound

Structure

NPC474291 OpenBabel07101718332D 23 24 0 0 1 0 0 0 0 0999 V2000 4.4495 2.2234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3385 0.8175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8569 -2.6200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6579 -2.7882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6253 0.7884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1020 1.5012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8265 -1.1084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3819 -2.2878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9805 -0.1604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9838 1.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0613 1.6830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4223 -2.2492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6355 -0.2300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4881 1.2638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2495 -1.8761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6764 0.7505 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.1204 1.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5906 -1.7690 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3764 0.8835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0773 -0.9573 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0747 -2.4616 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3913 1.4605 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 14 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 17 2 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 6 0 0 0 18 21 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 4 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	3.951
LogD:	3.247
LogS:	-4.165
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	5.566
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.54
MDCK Permeability:	2.482781383150723e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.183
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987
Plasma Protein Binding (PPB):	85.83232879638672%
Volume Distribution (VD):	1.065
Pgp-substrate:	10.300348281860352%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.328
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.506
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.356
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.791
CYP3A4-inhibitor:	0.678
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	9.203
Half-life (T1/2):	0.22

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.474
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.779
Carcinogencity:	0.273
Eye Corrosion:	0.026
Eye Irritation:	0.116
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC474291

Natural Product ID:	NPC474291
*Common Name:**	(3E,7S,11Z)-7-Hydroxy-3,11,15-Cembratrien-20,8-Olide
IUPAC Name:	(6E,10S,11R)-10-hydroxy-7,11-dimethyl-4-prop-1-en-2-yl-16-oxabicyclo[9.3.2]hexadeca-1(14),6-dien-15-one
Synonyms:
Standard InCHIKey:	MAFNJZZUTPINDH-BVQOYPTGSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-14(2)16-9-7-15(3)8-12-18(21)20(4)13-5-6-17(11-10-16)19(22)23-20/h6-7,16,18,21H,1,5,8-13H2,2-4H3/b15-7+/t16?,18-,20+/m0/s1
SMILES:	C/C/1=CCC(CCC2=CCC[C@@]([C@H](CC1)O)(C)OC2=O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464769
PubChem CID:	44584117
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO24413	Eunicea tourneforti	Species	Plexauridae	Eukaryota	n.a.	Caribbean	n.a.	PMID[7595587]
NPO24413	Eunicea tourneforti	Species	Plexauridae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	>	3000.0	ug ml-1	PMID[509314]

☑ 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 NPC474291 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	197
0.1-0.2	1193
0.2-0.3	4999
0.3-0.4	12410
0.4-0.5	12072
0.5-0.6	7094
0.6-0.7	3695
0.7-0.8	997
0.8-0.85	33
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.881	High Similarity	NPC153805
0.878	High Similarity	NPC9868
0.878	High Similarity	NPC70424
0.878	High Similarity	NPC243618
0.875	High Similarity	NPC233377
0.869	High Similarity	NPC248602
0.8588	High Similarity	NPC227379
0.8588	High Similarity	NPC281516
0.8588	High Similarity	NPC474471
0.8554	High Similarity	NPC72464
0.8452	Intermediate Similarity	NPC261380
0.8452	Intermediate Similarity	NPC137033
0.8434	Intermediate Similarity	NPC11620
0.8415	Intermediate Similarity	NPC325031
0.8395	Intermediate Similarity	NPC470244
0.8395	Intermediate Similarity	NPC470239
0.8391	Intermediate Similarity	NPC474761
0.8391	Intermediate Similarity	NPC476004
0.8391	Intermediate Similarity	NPC473448
0.8353	Intermediate Similarity	NPC164393
0.8295	Intermediate Similarity	NPC30515
0.8295	Intermediate Similarity	NPC303697
0.8289	Intermediate Similarity	NPC310210
0.8235	Intermediate Similarity	NPC99395
0.8235	Intermediate Similarity	NPC197903
0.8202	Intermediate Similarity	NPC81419
0.8202	Intermediate Similarity	NPC475912
0.8202	Intermediate Similarity	NPC469692
0.8202	Intermediate Similarity	NPC179746
0.8202	Intermediate Similarity	NPC469645
0.8182	Intermediate Similarity	NPC51004
0.8161	Intermediate Similarity	NPC202672
0.8148	Intermediate Similarity	NPC320630
0.8148	Intermediate Similarity	NPC116177
0.8148	Intermediate Similarity	NPC7563
0.814	Intermediate Similarity	NPC469483
0.814	Intermediate Similarity	NPC261721
0.814	Intermediate Similarity	NPC305475
0.814	Intermediate Similarity	NPC475461
0.8125	Intermediate Similarity	NPC329852
0.8118	Intermediate Similarity	NPC82297
0.8118	Intermediate Similarity	NPC474776
0.8111	Intermediate Similarity	NPC81386
0.8111	Intermediate Similarity	NPC474035
0.8111	Intermediate Similarity	NPC65829
0.8111	Intermediate Similarity	NPC121825
0.8095	Intermediate Similarity	NPC85772
0.809	Intermediate Similarity	NPC12172
0.809	Intermediate Similarity	NPC184463
0.809	Intermediate Similarity	NPC208886
0.8072	Intermediate Similarity	NPC103634
0.8068	Intermediate Similarity	NPC212598
0.8068	Intermediate Similarity	NPC307411
0.8049	Intermediate Similarity	NPC93763
0.8049	Intermediate Similarity	NPC267231
0.8049	Intermediate Similarity	NPC108816
0.8046	Intermediate Similarity	NPC474765
0.8023	Intermediate Similarity	NPC21469
0.8023	Intermediate Similarity	NPC165162
0.8023	Intermediate Similarity	NPC11804
0.8023	Intermediate Similarity	NPC255307
0.8023	Intermediate Similarity	NPC329749
0.8022	Intermediate Similarity	NPC270013
0.8022	Intermediate Similarity	NPC14961
0.8022	Intermediate Similarity	NPC36954
0.8022	Intermediate Similarity	NPC272050
0.8	Intermediate Similarity	NPC250315
0.8	Intermediate Similarity	NPC212486
0.8	Intermediate Similarity	NPC476300
0.7957	Intermediate Similarity	NPC187268
0.7952	Intermediate Similarity	NPC469617
0.7952	Intermediate Similarity	NPC89128
0.7935	Intermediate Similarity	NPC279621
0.7931	Intermediate Similarity	NPC475019
0.7931	Intermediate Similarity	NPC122502
0.7931	Intermediate Similarity	NPC474949
0.7931	Intermediate Similarity	NPC150755
0.7927	Intermediate Similarity	NPC180290
0.7927	Intermediate Similarity	NPC65603
0.7927	Intermediate Similarity	NPC476794
0.7927	Intermediate Similarity	NPC470240
0.7912	Intermediate Similarity	NPC71589
0.7907	Intermediate Similarity	NPC191476
0.7907	Intermediate Similarity	NPC114979
0.7907	Intermediate Similarity	NPC474780
0.7895	Intermediate Similarity	NPC86077
0.7889	Intermediate Similarity	NPC475972
0.7882	Intermediate Similarity	NPC94875
0.7882	Intermediate Similarity	NPC475159
0.7882	Intermediate Similarity	NPC65930
0.7882	Intermediate Similarity	NPC73310
0.7882	Intermediate Similarity	NPC89555
0.7882	Intermediate Similarity	NPC473712
0.7882	Intermediate Similarity	NPC473780
0.7882	Intermediate Similarity	NPC131002
0.7882	Intermediate Similarity	NPC473529
0.7882	Intermediate Similarity	NPC145914
0.7882	Intermediate Similarity	NPC329829
0.7882	Intermediate Similarity	NPC180363
0.7882	Intermediate Similarity	NPC11332
0.7872	Intermediate Similarity	NPC475053
0.7865	Intermediate Similarity	NPC295312
0.7865	Intermediate Similarity	NPC268298
0.7865	Intermediate Similarity	NPC474032
0.7865	Intermediate Similarity	NPC473564
0.7849	Intermediate Similarity	NPC40812
0.7848	Intermediate Similarity	NPC67183
0.7841	Intermediate Similarity	NPC160138
0.7841	Intermediate Similarity	NPC312561
0.7831	Intermediate Similarity	NPC471465
0.7831	Intermediate Similarity	NPC196653
0.7831	Intermediate Similarity	NPC128276
0.7826	Intermediate Similarity	NPC304886
0.7816	Intermediate Similarity	NPC86316
0.7816	Intermediate Similarity	NPC106416
0.7812	Intermediate Similarity	NPC475871
0.7812	Intermediate Similarity	NPC475945
0.7805	Intermediate Similarity	NPC235906
0.7805	Intermediate Similarity	NPC271070
0.7802	Intermediate Similarity	NPC162205
0.7802	Intermediate Similarity	NPC476049
0.7802	Intermediate Similarity	NPC475838
0.7802	Intermediate Similarity	NPC228451
0.7802	Intermediate Similarity	NPC125674
0.7802	Intermediate Similarity	NPC295204
0.7802	Intermediate Similarity	NPC273579
0.7802	Intermediate Similarity	NPC288240
0.7791	Intermediate Similarity	NPC169575
0.7791	Intermediate Similarity	NPC253801
0.7791	Intermediate Similarity	NPC144415
0.7791	Intermediate Similarity	NPC53867
0.7791	Intermediate Similarity	NPC44261
0.7791	Intermediate Similarity	NPC161045
0.7791	Intermediate Similarity	NPC473390
0.7791	Intermediate Similarity	NPC40746
0.7791	Intermediate Similarity	NPC131669
0.7791	Intermediate Similarity	NPC475947
0.7789	Intermediate Similarity	NPC46998
0.7789	Intermediate Similarity	NPC150923
0.7789	Intermediate Similarity	NPC185141
0.7789	Intermediate Similarity	NPC474742
0.7789	Intermediate Similarity	NPC110443
0.7789	Intermediate Similarity	NPC133907
0.7789	Intermediate Similarity	NPC128733
0.7778	Intermediate Similarity	NPC77337
0.7778	Intermediate Similarity	NPC476355
0.7778	Intermediate Similarity	NPC472966
0.7778	Intermediate Similarity	NPC129419
0.7778	Intermediate Similarity	NPC473619
0.7778	Intermediate Similarity	NPC265856
0.7778	Intermediate Similarity	NPC145666
0.7778	Intermediate Similarity	NPC475855
0.7778	Intermediate Similarity	NPC160540
0.7778	Intermediate Similarity	NPC166554
0.7766	Intermediate Similarity	NPC83895
0.7766	Intermediate Similarity	NPC473326
0.7766	Intermediate Similarity	NPC187761
0.7765	Intermediate Similarity	NPC112868
0.7765	Intermediate Similarity	NPC141810
0.7765	Intermediate Similarity	NPC25684
0.7765	Intermediate Similarity	NPC474894
0.7765	Intermediate Similarity	NPC281949
0.7765	Intermediate Similarity	NPC301477
0.7753	Intermediate Similarity	NPC476803
0.775	Intermediate Similarity	NPC163003
0.7742	Intermediate Similarity	NPC476315
0.7738	Intermediate Similarity	NPC98557
0.7738	Intermediate Similarity	NPC167881
0.7738	Intermediate Similarity	NPC617
0.7732	Intermediate Similarity	NPC100487
0.7727	Intermediate Similarity	NPC474762
0.7727	Intermediate Similarity	NPC476015
0.7727	Intermediate Similarity	NPC116575
0.7727	Intermediate Similarity	NPC311163
0.7727	Intermediate Similarity	NPC469910
0.7722	Intermediate Similarity	NPC101622
0.7722	Intermediate Similarity	NPC265574
0.7717	Intermediate Similarity	NPC477131
0.7717	Intermediate Similarity	NPC469632
0.7717	Intermediate Similarity	NPC474247
0.7711	Intermediate Similarity	NPC41780
0.7711	Intermediate Similarity	NPC40049
0.7711	Intermediate Similarity	NPC57744
0.7711	Intermediate Similarity	NPC187568
0.7708	Intermediate Similarity	NPC474747
0.7701	Intermediate Similarity	NPC163093
0.7701	Intermediate Similarity	NPC96259
0.7701	Intermediate Similarity	NPC476804
0.7701	Intermediate Similarity	NPC14575
0.7701	Intermediate Similarity	NPC156804
0.7701	Intermediate Similarity	NPC141193
0.7701	Intermediate Similarity	NPC156485
0.7701	Intermediate Similarity	NPC196487
0.7692	Intermediate Similarity	NPC177037
0.7692	Intermediate Similarity	NPC219874
0.7692	Intermediate Similarity	NPC473321
0.7692	Intermediate Similarity	NPC472814
0.7692	Intermediate Similarity	NPC470373
0.7692	Intermediate Similarity	NPC470379
0.7684	Intermediate Similarity	NPC288876

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 NPC474291 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1806
0.2-0.3	3672
0.3-0.4	2320
0.4-0.5	754
0.5-0.6	336
0.6-0.7	59
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
0.7978	Intermediate Similarity	NPD46	Approved
0.7978	Intermediate Similarity	NPD6698	Approved
0.7582	Intermediate Similarity	NPD7838	Discovery
0.7436	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6371	Approved
0.7273	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4225	Approved
0.7204	Intermediate Similarity	NPD5785	Approved
0.7191	Intermediate Similarity	NPD7154	Phase 3
0.7157	Intermediate Similarity	NPD6686	Approved
0.7128	Intermediate Similarity	NPD7983	Approved
0.7041	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD1694	Approved
0.7033	Intermediate Similarity	NPD5363	Approved
0.7	Intermediate Similarity	NPD5362	Discontinued
0.6915	Remote Similarity	NPD1695	Approved
0.69	Remote Similarity	NPD5344	Discontinued
0.6875	Remote Similarity	NPD3197	Phase 1
0.686	Remote Similarity	NPD8039	Approved
0.6848	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7115	Discovery
0.6778	Remote Similarity	NPD5369	Approved
0.6707	Remote Similarity	NPD7331	Phase 2
0.6703	Remote Similarity	NPD5209	Approved
0.6703	Remote Similarity	NPD4269	Approved
0.6703	Remote Similarity	NPD6435	Approved
0.6703	Remote Similarity	NPD4270	Approved
0.6701	Remote Similarity	NPD5778	Approved
0.6701	Remote Similarity	NPD5779	Approved
0.67	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4822	Approved
0.6636	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7640	Approved
0.6634	Remote Similarity	NPD7639	Approved
0.6604	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5786	Approved
0.6585	Remote Similarity	NPD7341	Phase 2
0.6574	Remote Similarity	NPD6053	Discontinued
0.6562	Remote Similarity	NPD6101	Approved
0.6562	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4756	Discovery
0.6484	Remote Similarity	NPD5368	Approved
0.6484	Remote Similarity	NPD4252	Approved
0.6471	Remote Similarity	NPD6648	Approved
0.6465	Remote Similarity	NPD7748	Approved
0.6452	Remote Similarity	NPD5332	Approved
0.6452	Remote Similarity	NPD5331	Approved
0.6444	Remote Similarity	NPD4268	Approved
0.6444	Remote Similarity	NPD4271	Approved
0.6436	Remote Similarity	NPD6084	Phase 2
0.6436	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD7515	Phase 2
0.6429	Remote Similarity	NPD6411	Approved
0.6421	Remote Similarity	NPD6684	Approved
0.6421	Remote Similarity	NPD7521	Approved
0.6421	Remote Similarity	NPD7334	Approved
0.6421	Remote Similarity	NPD6409	Approved
0.6421	Remote Similarity	NPD7146	Approved
0.6421	Remote Similarity	NPD5330	Approved
0.6413	Remote Similarity	NPD4790	Discontinued
0.64	Remote Similarity	NPD5695	Phase 3
0.6383	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD3665	Phase 1
0.6383	Remote Similarity	NPD3666	Approved
0.6383	Remote Similarity	NPD3133	Approved
0.6337	Remote Similarity	NPD7839	Suspended
0.633	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6903	Approved
0.6289	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6110	Phase 1
0.6275	Remote Similarity	NPD7902	Approved
0.6273	Remote Similarity	NPD8297	Approved
0.6263	Remote Similarity	NPD5693	Phase 1
0.6262	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD5279	Phase 3
0.625	Remote Similarity	NPD3618	Phase 1
0.625	Remote Similarity	NPD4249	Approved
0.6239	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD3172	Approved
0.6216	Remote Similarity	NPD4632	Approved
0.6214	Remote Similarity	NPD5696	Approved
0.6204	Remote Similarity	NPD6881	Approved
0.6204	Remote Similarity	NPD6899	Approved
0.6204	Remote Similarity	NPD6011	Approved
0.62	Remote Similarity	NPD6399	Phase 3
0.6186	Remote Similarity	NPD4251	Approved
0.6186	Remote Similarity	NPD7507	Approved
0.6186	Remote Similarity	NPD3573	Approved
0.6186	Remote Similarity	NPD4250	Approved
0.617	Remote Similarity	NPD3667	Approved
0.617	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7128	Approved
0.6168	Remote Similarity	NPD5739	Approved
0.6168	Remote Similarity	NPD6675	Approved
0.6168	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD4266	Approved
0.6154	Remote Similarity	NPD3196	Approved
0.6154	Remote Similarity	NPD3194	Approved
0.6154	Remote Similarity	NPD3195	Phase 2
0.6147	Remote Similarity	NPD6014	Approved
0.6147	Remote Similarity	NPD6013	Approved
0.6147	Remote Similarity	NPD6012	Approved
0.6139	Remote Similarity	NPD5282	Discontinued
0.6129	Remote Similarity	NPD4695	Discontinued
0.6122	Remote Similarity	NPD5737	Approved
0.6122	Remote Similarity	NPD6672	Approved
0.6111	Remote Similarity	NPD6412	Phase 2
0.6111	Remote Similarity	NPD5701	Approved
0.61	Remote Similarity	NPD6079	Approved
0.6091	Remote Similarity	NPD7290	Approved
0.6091	Remote Similarity	NPD7102	Approved
0.6091	Remote Similarity	NPD6883	Approved
0.6082	Remote Similarity	NPD4519	Discontinued
0.6082	Remote Similarity	NPD4623	Approved
0.6082	Remote Similarity	NPD6422	Discontinued
0.6071	Remote Similarity	NPD7909	Approved
0.6061	Remote Similarity	NPD5370	Suspended
0.6061	Remote Similarity	NPD5328	Approved
0.6061	Remote Similarity	NPD4753	Phase 2
0.6055	Remote Similarity	NPD7320	Approved
0.605	Remote Similarity	NPD8273	Phase 1
0.6049	Remote Similarity	NPD6109	Phase 1
0.6042	Remote Similarity	NPD4786	Approved
0.604	Remote Similarity	NPD4202	Approved
0.6038	Remote Similarity	NPD7632	Discontinued
0.6036	Remote Similarity	NPD6847	Approved
0.6036	Remote Similarity	NPD8130	Phase 1
0.6036	Remote Similarity	NPD6869	Approved
0.6036	Remote Similarity	NPD6650	Approved
0.6036	Remote Similarity	NPD6617	Approved
0.6036	Remote Similarity	NPD6649	Approved
0.6034	Remote Similarity	NPD6319	Approved
0.6033	Remote Similarity	NPD7319	Approved
0.6024	Remote Similarity	NPD368	Approved
0.6019	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD7829	Approved
0.6017	Remote Similarity	NPD7642	Approved
0.6017	Remote Similarity	NPD7830	Approved
0.6	Remote Similarity	NPD4221	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD4223	Phase 3
0.6	Remote Similarity	NPD6373	Approved
0.5983	Remote Similarity	NPD8516	Approved
0.5983	Remote Similarity	NPD8515	Approved
0.5983	Remote Similarity	NPD8513	Phase 3
0.5983	Remote Similarity	NPD8517	Approved
0.5982	Remote Similarity	NPD6882	Approved
0.5981	Remote Similarity	NPD6647	Phase 2
0.598	Remote Similarity	NPD7900	Approved
0.598	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD6927	Phase 3
0.5965	Remote Similarity	NPD2629	Approved
0.5963	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5208	Approved
0.5952	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD3730	Approved
0.5949	Remote Similarity	NPD3728	Approved
0.5946	Remote Similarity	NPD6421	Discontinued
0.5941	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD7637	Suspended
0.5941	Remote Similarity	NPD5284	Approved
0.5941	Remote Similarity	NPD5281	Approved
0.593	Remote Similarity	NPD3704	Approved
0.5922	Remote Similarity	NPD4629	Approved
0.5922	Remote Similarity	NPD5210	Approved
0.5918	Remote Similarity	NPD5690	Phase 2
0.5914	Remote Similarity	NPD3732	Approved
0.5913	Remote Similarity	NPD6009	Approved
0.5909	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6051	Approved
0.59	Remote Similarity	NPD6673	Approved
0.59	Remote Similarity	NPD6080	Approved
0.59	Remote Similarity	NPD6904	Approved
0.5897	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5211	Phase 2
0.5882	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD4197	Approved
0.5875	Remote Similarity	NPD342	Phase 1
0.587	Remote Similarity	NPD6933	Approved
0.5865	Remote Similarity	NPD5221	Approved
0.5865	Remote Similarity	NPD5222	Approved
0.5865	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7327	Approved
0.5862	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7328	Approved
0.5862	Remote Similarity	NPD7641	Discontinued
0.5859	Remote Similarity	NPD7524	Approved
0.5849	Remote Similarity	NPD4696	Approved
0.5849	Remote Similarity	NPD5286	Approved
0.5849	Remote Similarity	NPD5285	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