NPASS Compound

Structure

NPC233332 OpenBabel07101719502D 25 26 0 0 1 0 0 0 0 0999 V2000 -5.5549 -2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 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 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 0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1235 -0.8912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5889 -2.4659 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 -0.8660 -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 -2.5981 -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 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 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 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 15 2 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 21 1 0 0 0 0 6 21 1 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 18 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 18 1 1 0 0 0 19 22 1 1 0 0 0 20 21 1 6 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 22 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.25
Volume:	387.78
LogP:	5.518
LogD:	4.059
LogS:	-4.878
# Rotatable Bonds:	6
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.505
Synthetic Accessibility Score:	4.719
Fsp3:	0.682
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.705
MDCK Permeability:	1.9279306798125617e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.844
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.158
Plasma Protein Binding (PPB):	90.50472259521484%
Volume Distribution (VD):	2.357
Pgp-substrate:	9.553471565246582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.105
CYP2C19-substrate:	0.646
CYP2C9-inhibitor:	0.178
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.264
CYP3A4-inhibitor:	0.808
CYP3A4-substrate:	0.367

ADMET: Excretion

Clearance (CL):	3.103
Half-life (T1/2):	0.202

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.726
Drug-inuced Liver Injury (DILI):	0.321
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.732
Carcinogencity:	0.823
Eye Corrosion:	0.868
Eye Irritation:	0.91
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC233332

Natural Product ID:	NPC233332
*Common Name:**	14,17-Epoxyloba-8,10,13(15)-Trien-18-Ol-18-Acetate
IUPAC Name:	2-[(2R)-5-[(1S,3R,4R)-4-ethenyl-4-methyl-3-prop-1-en-2-ylcyclohexyl]-3,6-dihydro-2H-pyran-2-yl]propan-2-yl acetate
Synonyms:
Standard InCHIKey:	ASFMVDIIZYGBKO-RYTRXMBJSA-N
Standard InCHI:	InChI=1S/C22H34O3/c1-8-22(7)12-11-17(13-19(22)15(2)3)18-9-10-20(24-14-18)21(5,6)25-16(4)23/h8-9,17,19-20H,1-2,10-14H2,3-7H3/t17-,19+,20+,22-/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@@H](C[C@@H]1C(=C)C)C1=CC[C@@H](OC1)C(OC(=O)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511452
PubChem CID:	10569626
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002872] Elemane sesquiterpenoids

*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
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22209732]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	Eukaryota	n.a.	Mindoro, Philippines	n.a.	PMID[9548875]
NPO26994	Lobophytum pauciflorum	Species	Alcyoniidae	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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	10.0	mm	PMID[507681]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	8.0	mm	PMID[507681]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	6.0	mm	PMID[507681]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	33.96	ug.mL-1	PMID[507681]

☑ 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 NPC233332 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	198
0.1-0.2	1266
0.2-0.3	4771
0.3-0.4	14350
0.4-0.5	9758
0.5-0.6	7680
0.6-0.7	4189
0.7-0.8	467
0.8-0.85	11
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9114	High Similarity	NPC49208
0.8875	High Similarity	NPC23748
0.8861	High Similarity	NPC25554
0.8846	High Similarity	NPC233295
0.8608	High Similarity	NPC242767
0.8488	Intermediate Similarity	NPC303697
0.8452	Intermediate Similarity	NPC131329
0.8434	Intermediate Similarity	NPC35933
0.8293	Intermediate Similarity	NPC471218
0.8272	Intermediate Similarity	NPC469802
0.8272	Intermediate Similarity	NPC474592
0.8256	Intermediate Similarity	NPC20946
0.8256	Intermediate Similarity	NPC246028
0.8205	Intermediate Similarity	NPC104644
0.8161	Intermediate Similarity	NPC273199
0.814	Intermediate Similarity	NPC473879
0.8095	Intermediate Similarity	NPC96055
0.8068	Intermediate Similarity	NPC177641
0.8046	Intermediate Similarity	NPC177141
0.8046	Intermediate Similarity	NPC82876
0.8025	Intermediate Similarity	NPC184737
0.8023	Intermediate Similarity	NPC245004
0.8023	Intermediate Similarity	NPC166857
0.8	Intermediate Similarity	NPC472442
0.8	Intermediate Similarity	NPC474013
0.8	Intermediate Similarity	NPC471795
0.7973	Intermediate Similarity	NPC329698
0.7931	Intermediate Similarity	NPC93411
0.7931	Intermediate Similarity	NPC477128
0.7927	Intermediate Similarity	NPC44083
0.7927	Intermediate Similarity	NPC153987
0.7927	Intermediate Similarity	NPC100906
0.7907	Intermediate Similarity	NPC471219
0.7907	Intermediate Similarity	NPC102996
0.7907	Intermediate Similarity	NPC286153
0.7907	Intermediate Similarity	NPC220478
0.7901	Intermediate Similarity	NPC283619
0.7889	Intermediate Similarity	NPC166143
0.7889	Intermediate Similarity	NPC120351
0.7889	Intermediate Similarity	NPC471994
0.7882	Intermediate Similarity	NPC306951
0.7857	Intermediate Similarity	NPC256112
0.7841	Intermediate Similarity	NPC293044
0.7841	Intermediate Similarity	NPC284561
0.7831	Intermediate Similarity	NPC195424
0.7816	Intermediate Similarity	NPC102640
0.7816	Intermediate Similarity	NPC476600
0.7805	Intermediate Similarity	NPC474005
0.7802	Intermediate Similarity	NPC33473
0.7802	Intermediate Similarity	NPC281134
0.7792	Intermediate Similarity	NPC476945
0.7778	Intermediate Similarity	NPC301525
0.7778	Intermediate Similarity	NPC53555
0.7765	Intermediate Similarity	NPC193198
0.7765	Intermediate Similarity	NPC12283
0.7765	Intermediate Similarity	NPC472440
0.7765	Intermediate Similarity	NPC476927
0.7765	Intermediate Similarity	NPC42476
0.7765	Intermediate Similarity	NPC477124
0.7765	Intermediate Similarity	NPC311070
0.7765	Intermediate Similarity	NPC474193
0.7753	Intermediate Similarity	NPC469595
0.7753	Intermediate Similarity	NPC212679
0.7753	Intermediate Similarity	NPC220454
0.7753	Intermediate Similarity	NPC78973
0.7738	Intermediate Similarity	NPC14203
0.7738	Intermediate Similarity	NPC170303
0.7738	Intermediate Similarity	NPC229584
0.7738	Intermediate Similarity	NPC142163
0.7738	Intermediate Similarity	NPC108476
0.7727	Intermediate Similarity	NPC106332
0.7727	Intermediate Similarity	NPC69713
0.7727	Intermediate Similarity	NPC24816
0.7701	Intermediate Similarity	NPC329692
0.7701	Intermediate Similarity	NPC118266
0.7692	Intermediate Similarity	NPC104925
0.7692	Intermediate Similarity	NPC469491
0.7692	Intermediate Similarity	NPC472360
0.7692	Intermediate Similarity	NPC88507
0.7692	Intermediate Similarity	NPC472416
0.7692	Intermediate Similarity	NPC298973
0.7692	Intermediate Similarity	NPC469697
0.7692	Intermediate Similarity	NPC38830
0.7684	Intermediate Similarity	NPC11956
0.7683	Intermediate Similarity	NPC40049
0.7683	Intermediate Similarity	NPC470751
0.7683	Intermediate Similarity	NPC189206
0.7683	Intermediate Similarity	NPC470750
0.7674	Intermediate Similarity	NPC318515
0.7667	Intermediate Similarity	NPC49420
0.7667	Intermediate Similarity	NPC234335
0.7667	Intermediate Similarity	NPC477574
0.766	Intermediate Similarity	NPC473510
0.766	Intermediate Similarity	NPC38855
0.7647	Intermediate Similarity	NPC471159
0.7647	Intermediate Similarity	NPC123880
0.7647	Intermediate Similarity	NPC471408
0.764	Intermediate Similarity	NPC261320
0.764	Intermediate Similarity	NPC473647
0.7634	Intermediate Similarity	NPC125551
0.7634	Intermediate Similarity	NPC239547
0.7634	Intermediate Similarity	NPC155319
0.7634	Intermediate Similarity	NPC473244
0.7634	Intermediate Similarity	NPC96597
0.7634	Intermediate Similarity	NPC309503
0.7634	Intermediate Similarity	NPC210337
0.7634	Intermediate Similarity	NPC91197
0.7619	Intermediate Similarity	NPC268827
0.7619	Intermediate Similarity	NPC474739
0.7619	Intermediate Similarity	NPC269791
0.7614	Intermediate Similarity	NPC471796
0.7609	Intermediate Similarity	NPC472189
0.7609	Intermediate Similarity	NPC471362
0.7609	Intermediate Similarity	NPC471372
0.7609	Intermediate Similarity	NPC276110
0.7604	Intermediate Similarity	NPC23584
0.7595	Intermediate Similarity	NPC469660
0.759	Intermediate Similarity	NPC264610
0.7586	Intermediate Similarity	NPC189311
0.7582	Intermediate Similarity	NPC7349
0.7579	Intermediate Similarity	NPC472554
0.7558	Intermediate Similarity	NPC132386
0.7558	Intermediate Similarity	NPC474809
0.7558	Intermediate Similarity	NPC22611
0.7558	Intermediate Similarity	NPC222358
0.7556	Intermediate Similarity	NPC220216
0.7556	Intermediate Similarity	NPC469372
0.7556	Intermediate Similarity	NPC302280
0.7556	Intermediate Similarity	NPC310479
0.7556	Intermediate Similarity	NPC182136
0.7553	Intermediate Similarity	NPC98868
0.7532	Intermediate Similarity	NPC185587
0.7531	Intermediate Similarity	NPC475517
0.7531	Intermediate Similarity	NPC474524
0.7531	Intermediate Similarity	NPC71152
0.7529	Intermediate Similarity	NPC195334
0.7529	Intermediate Similarity	NPC290495
0.7529	Intermediate Similarity	NPC327002
0.7529	Intermediate Similarity	NPC159148
0.7529	Intermediate Similarity	NPC476101
0.7528	Intermediate Similarity	NPC215831
0.7528	Intermediate Similarity	NPC226863
0.7527	Intermediate Similarity	NPC221801
0.7527	Intermediate Similarity	NPC162346
0.7527	Intermediate Similarity	NPC311166
0.7527	Intermediate Similarity	NPC284194
0.7527	Intermediate Similarity	NPC171598
0.7527	Intermediate Similarity	NPC471765
0.7527	Intermediate Similarity	NPC88009
0.7527	Intermediate Similarity	NPC57664
0.7527	Intermediate Similarity	NPC211810
0.75	Intermediate Similarity	NPC471537
0.75	Intermediate Similarity	NPC325869
0.75	Intermediate Similarity	NPC477129
0.75	Intermediate Similarity	NPC140277
0.75	Intermediate Similarity	NPC105490
0.75	Intermediate Similarity	NPC175145
0.75	Intermediate Similarity	NPC264127
0.75	Intermediate Similarity	NPC475069
0.75	Intermediate Similarity	NPC477130
0.75	Intermediate Similarity	NPC472552
0.75	Intermediate Similarity	NPC477084
0.75	Intermediate Similarity	NPC131813
0.7474	Intermediate Similarity	NPC230546
0.7474	Intermediate Similarity	NPC227865
0.7473	Intermediate Similarity	NPC329842
0.7473	Intermediate Similarity	NPC124374
0.7471	Intermediate Similarity	NPC102048
0.747	Intermediate Similarity	NPC476439
0.747	Intermediate Similarity	NPC132542
0.7468	Intermediate Similarity	NPC269841
0.7468	Intermediate Similarity	NPC101622
0.7468	Intermediate Similarity	NPC329656
0.7447	Intermediate Similarity	NPC472188
0.7447	Intermediate Similarity	NPC110937
0.7447	Intermediate Similarity	NPC202705
0.7447	Intermediate Similarity	NPC73911
0.7447	Intermediate Similarity	NPC98112
0.7444	Intermediate Similarity	NPC470734
0.7444	Intermediate Similarity	NPC50488
0.7444	Intermediate Similarity	NPC474396
0.7444	Intermediate Similarity	NPC73995
0.7442	Intermediate Similarity	NPC286786
0.7442	Intermediate Similarity	NPC16321
0.7442	Intermediate Similarity	NPC2524
0.7442	Intermediate Similarity	NPC200513
0.7442	Intermediate Similarity	NPC178676
0.7442	Intermediate Similarity	NPC155521
0.7439	Intermediate Similarity	NPC113639
0.7436	Intermediate Similarity	NPC474477
0.7436	Intermediate Similarity	NPC472266
0.7423	Intermediate Similarity	NPC297617
0.7419	Intermediate Similarity	NPC476519
0.7416	Intermediate Similarity	NPC471779
0.7416	Intermediate Similarity	NPC171722
0.7416	Intermediate Similarity	NPC476948
0.7416	Intermediate Similarity	NPC125925
0.7416	Intermediate Similarity	NPC312561
0.7416	Intermediate Similarity	NPC128644
0.7416	Intermediate Similarity	NPC473891

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 NPC233332 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1474
0.2-0.3	3925
0.3-0.4	2350
0.4-0.5	807
0.5-0.6	332
0.6-0.7	79
0.7-0.8	3
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
0.7841	Intermediate Similarity	NPD6051	Approved
0.7442	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8039	Approved
0.7191	Intermediate Similarity	NPD1694	Approved
0.7188	Intermediate Similarity	NPD4225	Approved
0.7179	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5330	Approved
0.7111	Intermediate Similarity	NPD6409	Approved
0.7111	Intermediate Similarity	NPD7146	Approved
0.7111	Intermediate Similarity	NPD7521	Approved
0.7111	Intermediate Similarity	NPD7334	Approved
0.7111	Intermediate Similarity	NPD6684	Approved
0.701	Intermediate Similarity	NPD7638	Approved
0.6957	Remote Similarity	NPD6903	Approved
0.6957	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7640	Approved
0.6939	Remote Similarity	NPD6648	Approved
0.6939	Remote Similarity	NPD7639	Approved
0.6916	Remote Similarity	NPD7115	Discovery
0.6889	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5344	Discontinued
0.6842	Remote Similarity	NPD6399	Phase 3
0.6774	Remote Similarity	NPD6672	Approved
0.6774	Remote Similarity	NPD5737	Approved
0.6744	Remote Similarity	NPD6933	Approved
0.6739	Remote Similarity	NPD6098	Approved
0.6737	Remote Similarity	NPD7637	Suspended
0.6737	Remote Similarity	NPD5693	Phase 1
0.6706	Remote Similarity	NPD6926	Approved
0.6706	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6635	Remote Similarity	NPD6686	Approved
0.6632	Remote Similarity	NPD7838	Discovery
0.6628	Remote Similarity	NPD7339	Approved
0.6628	Remote Similarity	NPD8264	Approved
0.6628	Remote Similarity	NPD6942	Approved
0.6598	Remote Similarity	NPD7748	Approved
0.6598	Remote Similarity	NPD7900	Approved
0.6598	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6695	Phase 3
0.6591	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6411	Approved
0.6552	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6904	Approved
0.6526	Remote Similarity	NPD6673	Approved
0.6526	Remote Similarity	NPD6080	Approved
0.6522	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4786	Approved
0.6518	Remote Similarity	NPD7503	Approved
0.6517	Remote Similarity	NPD7645	Phase 2
0.6512	Remote Similarity	NPD4784	Approved
0.6512	Remote Similarity	NPD4785	Approved
0.65	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5778	Approved
0.6495	Remote Similarity	NPD5779	Approved
0.6484	Remote Similarity	NPD5209	Approved
0.6484	Remote Similarity	NPD3667	Approved
0.6465	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6698	Approved
0.6458	Remote Similarity	NPD46	Approved
0.6458	Remote Similarity	NPD5207	Approved
0.6444	Remote Similarity	NPD7514	Phase 3
0.6444	Remote Similarity	NPD6931	Approved
0.6444	Remote Similarity	NPD7332	Phase 2
0.6444	Remote Similarity	NPD6930	Phase 2
0.6444	Remote Similarity	NPD7525	Registered
0.6421	Remote Similarity	NPD5208	Approved
0.64	Remote Similarity	NPD7902	Approved
0.64	Remote Similarity	NPD6083	Phase 2
0.64	Remote Similarity	NPD6084	Phase 2
0.6396	Remote Similarity	NPD7328	Approved
0.6396	Remote Similarity	NPD7327	Approved
0.6392	Remote Similarity	NPD7515	Phase 2
0.6392	Remote Similarity	NPD5694	Approved
0.6392	Remote Similarity	NPD6050	Approved
0.6381	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD8033	Approved
0.6364	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5695	Phase 3
0.6354	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6101	Approved
0.6353	Remote Similarity	NPD7143	Approved
0.6353	Remote Similarity	NPD7144	Approved
0.6344	Remote Similarity	NPD3668	Phase 3
0.6339	Remote Similarity	NPD7516	Approved
0.6333	Remote Similarity	NPD6929	Approved
0.6333	Remote Similarity	NPD4195	Approved
0.6316	Remote Similarity	NPD7750	Discontinued
0.6316	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7632	Discontinued
0.6292	Remote Similarity	NPD6932	Approved
0.6289	Remote Similarity	NPD5692	Phase 3
0.6289	Remote Similarity	NPD5785	Approved
0.6283	Remote Similarity	NPD8377	Approved
0.6283	Remote Similarity	NPD8294	Approved
0.6279	Remote Similarity	NPD7152	Approved
0.6279	Remote Similarity	NPD7150	Approved
0.6279	Remote Similarity	NPD7151	Approved
0.6279	Remote Similarity	NPD4243	Approved
0.6277	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4821	Approved
0.6264	Remote Similarity	NPD4819	Approved
0.6264	Remote Similarity	NPD7509	Discontinued
0.6264	Remote Similarity	NPD4822	Approved
0.6264	Remote Similarity	NPD4820	Approved
0.6264	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1145	Discontinued
0.6239	Remote Similarity	NPD8297	Approved
0.6239	Remote Similarity	NPD6053	Discontinued
0.6237	Remote Similarity	NPD5362	Discontinued
0.6237	Remote Similarity	NPD7154	Phase 3
0.6235	Remote Similarity	NPD6923	Approved
0.6235	Remote Similarity	NPD6922	Approved
0.6228	Remote Similarity	NPD8378	Approved
0.6228	Remote Similarity	NPD8296	Approved
0.6228	Remote Similarity	NPD8380	Approved
0.6228	Remote Similarity	NPD8335	Approved
0.6228	Remote Similarity	NPD8379	Approved
0.6222	Remote Similarity	NPD7145	Approved
0.6222	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4623	Approved
0.6211	Remote Similarity	NPD4519	Discontinued
0.6204	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6902	Approved
0.6176	Remote Similarity	NPD5696	Approved
0.617	Remote Similarity	NPD3665	Phase 1
0.617	Remote Similarity	NPD3666	Approved
0.617	Remote Similarity	NPD3133	Approved
0.6168	Remote Similarity	NPD6881	Approved
0.6168	Remote Similarity	NPD6899	Approved
0.6168	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6675	Approved
0.6132	Remote Similarity	NPD7128	Approved
0.6132	Remote Similarity	NPD5739	Approved
0.6132	Remote Similarity	NPD6008	Approved
0.6132	Remote Similarity	NPD6402	Approved
0.6111	Remote Similarity	NPD5776	Phase 2
0.6111	Remote Similarity	NPD6925	Approved
0.6105	Remote Similarity	NPD6893	Approved
0.6105	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6001	Approved
0.61	Remote Similarity	NPD5707	Approved
0.6075	Remote Similarity	NPD5697	Approved
0.6064	Remote Similarity	NPD5331	Approved
0.6064	Remote Similarity	NPD5332	Approved
0.6061	Remote Similarity	NPD8034	Phase 2
0.6061	Remote Similarity	NPD7983	Approved
0.6061	Remote Similarity	NPD8035	Phase 2
0.6061	Remote Similarity	NPD5281	Approved
0.6061	Remote Similarity	NPD7087	Discontinued
0.6061	Remote Similarity	NPD5284	Approved
0.6061	Remote Similarity	NPD6079	Approved
0.6058	Remote Similarity	NPD4159	Approved
0.6055	Remote Similarity	NPD7290	Approved
0.6055	Remote Similarity	NPD6883	Approved
0.6055	Remote Similarity	NPD6371	Approved
0.6055	Remote Similarity	NPD7102	Approved
0.6044	Remote Similarity	NPD4268	Approved
0.6044	Remote Similarity	NPD4271	Approved
0.6042	Remote Similarity	NPD3618	Phase 1
0.604	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6898	Phase 1
0.6022	Remote Similarity	NPD4790	Discontinued
0.6022	Remote Similarity	NPD5369	Approved
0.602	Remote Similarity	NPD1695	Approved
0.602	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5328	Approved
0.6019	Remote Similarity	NPD7320	Approved
0.6019	Remote Similarity	NPD6011	Approved
0.6018	Remote Similarity	NPD4198	Discontinued
0.6017	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6847	Approved
0.5978	Remote Similarity	NPD6683	Phase 2
0.5976	Remote Similarity	NPD4194	Approved
0.5976	Remote Similarity	NPD368	Approved
0.5976	Remote Similarity	NPD4193	Approved
0.5976	Remote Similarity	NPD4192	Approved
0.5976	Remote Similarity	NPD4191	Approved
0.5963	Remote Similarity	NPD6013	Approved
0.5963	Remote Similarity	NPD6012	Approved
0.5963	Remote Similarity	NPD6373	Approved
0.5963	Remote Similarity	NPD6372	Approved
0.5963	Remote Similarity	NPD6014	Approved
0.5957	Remote Similarity	NPD4221	Approved
0.5957	Remote Similarity	NPD4269	Approved
0.5957	Remote Similarity	NPD4223	Phase 3
0.5957	Remote Similarity	NPD4270	Approved
0.5946	Remote Similarity	NPD6882	Approved
0.5938	Remote Similarity	NPD5329	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