NPASS Compound

Structure

NPC239373 OpenBabel07101718312D 22 23 0 0 1 0 0 0 0 0999 V2000 2.1906 3.7470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9227 3.7470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2222 0.7225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -3.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4511 1.3110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8134 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2473 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0316 -2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8134 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0316 2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2999 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2999 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 3.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2473 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -2.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 2.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 2.0245 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6479 2.9254 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 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 17 18 1 0 0 0 0 18 21 1 6 0 0 0 19 20 1 6 0 0 0 19 22 1 0 0 0 0 20 5 1 6 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	347.034
LogP:	4.196
LogD:	3.867
LogS:	-4.124
# Rotatable Bonds:	1
TPSA:	32.76
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.549
Synthetic Accessibility Score:	4.724
Fsp3:	0.7
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:	-4.472
MDCK Permeability:	3.134140933980234e-05
Pgp-inhibitor:	0.944
Pgp-substrate:	0.784
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.149
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.435
Plasma Protein Binding (PPB):	97.92862701416016%
Volume Distribution (VD):	1.874
Pgp-substrate:	2.921588659286499%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.222
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.134
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.398
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.668
CYP3A4-substrate:	0.435

ADMET: Excretion

Clearance (CL):	9.108
Half-life (T1/2):	0.118

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.117
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.874
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.773
Carcinogencity:	0.849
Eye Corrosion:	0.033
Eye Irritation:	0.185
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC239373

Natural Product ID:	NPC239373
*Common Name:**	(1Z,3E,7E,11S, 12S,14S)-11,12-Epoxy Cembra-1,3,7-Trien-14-Ol
IUPAC Name:	(1S,4E,8E,10Z,12S,14S)-4,8,14-trimethyl-11-propan-2-yl-15-oxabicyclo[12.1.0]pentadeca-4,8,10-trien-12-ol
Synonyms:
Standard InCHIKey:	NPSBLVCLWPSNIZ-XHQPGYRNSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-14(2)17-11-9-15(3)7-6-8-16(4)10-12-19-20(5,22-19)13-18(17)21/h8-9,11,14,18-19,21H,6-7,10,12-13H2,1-5H3/b15-9+,16-8+,17-11-/t18-,19-,20-/m0/s1
SMILES:	CC(C)/C/1=C/C=C(C)/CC/C=C(C)/CC[C@H]2[C@](C)(C[C@@H]1O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486587
PubChem CID:	23424635
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] 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
NPO21438	Cladiella kashmani	Species	Alcyoniidae	Eukaryota	n.a.	African soft coral	n.a.	PMID[11087607]
NPO21438	Cladiella kashmani	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	50.0	ppm	PMID[453240]

☑ 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 NPC239373 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	185
0.1-0.2	1590
0.2-0.3	6380
0.3-0.4	17590
0.4-0.5	10315
0.5-0.6	5370
0.6-0.7	1112
0.7-0.8	136
0.8-0.85	12
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC329989
0.8806	High Similarity	NPC259299
0.8676	High Similarity	NPC305698
0.8551	High Similarity	NPC304690
0.8551	High Similarity	NPC74722
0.8507	High Similarity	NPC308844
0.8493	Intermediate Similarity	NPC476703
0.8451	Intermediate Similarity	NPC329763
0.8333	Intermediate Similarity	NPC471525
0.8333	Intermediate Similarity	NPC190859
0.8308	Intermediate Similarity	NPC475931
0.8308	Intermediate Similarity	NPC122239
0.8289	Intermediate Similarity	NPC474894
0.8194	Intermediate Similarity	NPC476709
0.8182	Intermediate Similarity	NPC127824
0.8154	Intermediate Similarity	NPC226848
0.8133	Intermediate Similarity	NPC477089
0.8108	Intermediate Similarity	NPC170148
0.8088	Intermediate Similarity	NPC300593
0.8026	Intermediate Similarity	NPC471537
0.8	Intermediate Similarity	NPC73603
0.7969	Intermediate Similarity	NPC223604
0.7917	Intermediate Similarity	NPC129630
0.7879	Intermediate Similarity	NPC181872
0.7867	Intermediate Similarity	NPC271070
0.7867	Intermediate Similarity	NPC301525
0.7838	Intermediate Similarity	NPC144995
0.7838	Intermediate Similarity	NPC227814
0.7794	Intermediate Similarity	NPC225342
0.7778	Intermediate Similarity	NPC329656
0.7763	Intermediate Similarity	NPC84360
0.7722	Intermediate Similarity	NPC477390
0.7722	Intermediate Similarity	NPC477385
0.7711	Intermediate Similarity	NPC128066
0.7703	Intermediate Similarity	NPC130665
0.7692	Intermediate Similarity	NPC329686
0.7671	Intermediate Similarity	NPC4299
0.7662	Intermediate Similarity	NPC68119
0.7662	Intermediate Similarity	NPC13823
0.7656	Intermediate Similarity	NPC474496
0.7654	Intermediate Similarity	NPC298595
0.7647	Intermediate Similarity	NPC66020
0.7647	Intermediate Similarity	NPC99487
0.7647	Intermediate Similarity	NPC240506
0.7639	Intermediate Similarity	NPC224532
0.7632	Intermediate Similarity	NPC268111
0.7619	Intermediate Similarity	NPC191323
0.7606	Intermediate Similarity	NPC267027
0.7571	Intermediate Similarity	NPC309300
0.7568	Intermediate Similarity	NPC471662
0.7564	Intermediate Similarity	NPC476701
0.7561	Intermediate Similarity	NPC281316
0.7536	Intermediate Similarity	NPC68679
0.7536	Intermediate Similarity	NPC207007
0.7536	Intermediate Similarity	NPC475251
0.7536	Intermediate Similarity	NPC321867
0.7534	Intermediate Similarity	NPC90115
0.7534	Intermediate Similarity	NPC101622
0.7534	Intermediate Similarity	NPC217570
0.7532	Intermediate Similarity	NPC476439
0.7532	Intermediate Similarity	NPC477425
0.7532	Intermediate Similarity	NPC40049
0.7532	Intermediate Similarity	NPC477427
0.7532	Intermediate Similarity	NPC477426
0.7532	Intermediate Similarity	NPC474826
0.75	Intermediate Similarity	NPC278895
0.75	Intermediate Similarity	NPC472255
0.75	Intermediate Similarity	NPC472253
0.75	Intermediate Similarity	NPC143810
0.75	Intermediate Similarity	NPC83838
0.7465	Intermediate Similarity	NPC19569
0.7463	Intermediate Similarity	NPC52012
0.7436	Intermediate Similarity	NPC475980
0.7436	Intermediate Similarity	NPC474005
0.7436	Intermediate Similarity	NPC476314
0.7432	Intermediate Similarity	NPC470041
0.7432	Intermediate Similarity	NPC34834
0.7429	Intermediate Similarity	NPC473508
0.7407	Intermediate Similarity	NPC231601
0.7403	Intermediate Similarity	NPC256720
0.7403	Intermediate Similarity	NPC236228
0.7403	Intermediate Similarity	NPC471658
0.7397	Intermediate Similarity	NPC167527
0.7375	Intermediate Similarity	NPC112868
0.7368	Intermediate Similarity	NPC471659
0.7361	Intermediate Similarity	NPC272125
0.7361	Intermediate Similarity	NPC311736
0.7353	Intermediate Similarity	NPC155025
0.7349	Intermediate Similarity	NPC477389
0.7349	Intermediate Similarity	NPC477387
0.7349	Intermediate Similarity	NPC61527
0.7344	Intermediate Similarity	NPC473672
0.7344	Intermediate Similarity	NPC474495
0.7342	Intermediate Similarity	NPC325869
0.7333	Intermediate Similarity	NPC472254
0.7333	Intermediate Similarity	NPC23954
0.7324	Intermediate Similarity	NPC140233
0.7324	Intermediate Similarity	NPC287744
0.7317	Intermediate Similarity	NPC474047
0.7297	Intermediate Similarity	NPC16964
0.7297	Intermediate Similarity	NPC471560
0.7297	Intermediate Similarity	NPC269841
0.7294	Intermediate Similarity	NPC49783
0.7284	Intermediate Similarity	NPC155521
0.7273	Intermediate Similarity	NPC319090
0.7273	Intermediate Similarity	NPC328104
0.7273	Intermediate Similarity	NPC23231
0.7273	Intermediate Similarity	NPC60818
0.7262	Intermediate Similarity	NPC477386
0.7262	Intermediate Similarity	NPC477388
0.726	Intermediate Similarity	NPC477791
0.726	Intermediate Similarity	NPC163290
0.726	Intermediate Similarity	NPC69649
0.726	Intermediate Similarity	NPC114651
0.726	Intermediate Similarity	NPC68703
0.726	Intermediate Similarity	NPC136813
0.726	Intermediate Similarity	NPC82337
0.725	Intermediate Similarity	NPC324772
0.7237	Intermediate Similarity	NPC68443
0.7237	Intermediate Similarity	NPC265485
0.7237	Intermediate Similarity	NPC477085
0.7237	Intermediate Similarity	NPC220939
0.7222	Intermediate Similarity	NPC471200
0.7222	Intermediate Similarity	NPC61503
0.7215	Intermediate Similarity	NPC4436
0.72	Intermediate Similarity	NPC473361
0.72	Intermediate Similarity	NPC329904
0.72	Intermediate Similarity	NPC475310
0.7195	Intermediate Similarity	NPC475989
0.7195	Intermediate Similarity	NPC475789
0.7188	Intermediate Similarity	NPC182102
0.7188	Intermediate Similarity	NPC26960
0.7183	Intermediate Similarity	NPC474155
0.7183	Intermediate Similarity	NPC473759
0.7179	Intermediate Similarity	NPC469880
0.7179	Intermediate Similarity	NPC310643
0.7164	Intermediate Similarity	NPC148163
0.7164	Intermediate Similarity	NPC130209
0.7164	Intermediate Similarity	NPC227135
0.7164	Intermediate Similarity	NPC281590
0.7164	Intermediate Similarity	NPC148216
0.7162	Intermediate Similarity	NPC272961
0.7162	Intermediate Similarity	NPC470040
0.7162	Intermediate Similarity	NPC471238
0.716	Intermediate Similarity	NPC246621
0.716	Intermediate Similarity	NPC315731
0.716	Intermediate Similarity	NPC320525
0.7143	Intermediate Similarity	NPC471081
0.7143	Intermediate Similarity	NPC329090
0.7143	Intermediate Similarity	NPC201048
0.7143	Intermediate Similarity	NPC476366
0.7143	Intermediate Similarity	NPC258788
0.7143	Intermediate Similarity	NPC255143
0.7143	Intermediate Similarity	NPC24590
0.7143	Intermediate Similarity	NPC306727
0.7143	Intermediate Similarity	NPC27395
0.7126	Intermediate Similarity	NPC476705
0.7125	Intermediate Similarity	NPC31258
0.7123	Intermediate Similarity	NPC230107
0.7123	Intermediate Similarity	NPC326310
0.7123	Intermediate Similarity	NPC469328
0.7123	Intermediate Similarity	NPC202017
0.7108	Intermediate Similarity	NPC186155
0.7108	Intermediate Similarity	NPC78673
0.7108	Intermediate Similarity	NPC160517
0.7105	Intermediate Similarity	NPC477086
0.7105	Intermediate Similarity	NPC471272
0.7105	Intermediate Similarity	NPC477084
0.7105	Intermediate Similarity	NPC477087
0.7089	Intermediate Similarity	NPC471454
0.7089	Intermediate Similarity	NPC470711
0.7089	Intermediate Similarity	NPC470758
0.7089	Intermediate Similarity	NPC315394
0.7089	Intermediate Similarity	NPC476007
0.7083	Intermediate Similarity	NPC110241
0.7083	Intermediate Similarity	NPC225415
0.7073	Intermediate Similarity	NPC259858
0.7067	Intermediate Similarity	NPC472947
0.7059	Intermediate Similarity	NPC24443
0.7051	Intermediate Similarity	NPC69383
0.7051	Intermediate Similarity	NPC171148
0.7051	Intermediate Similarity	NPC133580
0.7051	Intermediate Similarity	NPC313179
0.7051	Intermediate Similarity	NPC113639
0.7051	Intermediate Similarity	NPC32832
0.7042	Intermediate Similarity	NPC210346
0.7037	Intermediate Similarity	NPC474592
0.7037	Intermediate Similarity	NPC474739
0.7027	Intermediate Similarity	NPC161612
0.7027	Intermediate Similarity	NPC193029
0.7027	Intermediate Similarity	NPC33583
0.7027	Intermediate Similarity	NPC473357
0.7024	Intermediate Similarity	NPC474349
0.7024	Intermediate Similarity	NPC474189
0.7011	Intermediate Similarity	NPC477865
0.7011	Intermediate Similarity	NPC469403
0.7011	Intermediate Similarity	NPC477866
0.7011	Intermediate Similarity	NPC3952
0.7	Intermediate Similarity	NPC57664
0.7	Intermediate Similarity	NPC470944

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 NPC239373 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	2122
0.2-0.3	3926
0.3-0.4	2134
0.4-0.5	641
0.5-0.6	107
0.6-0.7	40
0.7-0.8	5
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
0.7536	Intermediate Similarity	NPD368	Approved
0.7531	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6695	Phase 3
0.725	Intermediate Similarity	NPD6930	Phase 2
0.725	Intermediate Similarity	NPD6931	Approved
0.7209	Intermediate Similarity	NPD7838	Discovery
0.7164	Intermediate Similarity	NPD342	Phase 1
0.7143	Intermediate Similarity	NPD6924	Approved
0.7143	Intermediate Similarity	NPD6926	Approved
0.7125	Intermediate Similarity	NPD6929	Approved
0.7059	Intermediate Similarity	NPD7750	Discontinued
0.7059	Intermediate Similarity	NPD7524	Approved
0.7051	Intermediate Similarity	NPD8264	Approved
0.7037	Intermediate Similarity	NPD7332	Phase 2
0.7037	Intermediate Similarity	NPD7514	Phase 3
0.7	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6933	Approved
0.6951	Remote Similarity	NPD6902	Approved
0.6875	Remote Similarity	NPD6925	Approved
0.6875	Remote Similarity	NPD5776	Phase 2
0.6829	Remote Similarity	NPD4822	Approved
0.6829	Remote Similarity	NPD7509	Discontinued
0.6829	Remote Similarity	NPD4820	Approved
0.6829	Remote Similarity	NPD4821	Approved
0.6829	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4819	Approved
0.6824	Remote Similarity	NPD6893	Approved
0.6795	Remote Similarity	NPD4732	Discontinued
0.679	Remote Similarity	NPD7145	Approved
0.6786	Remote Similarity	NPD7154	Phase 3
0.6747	Remote Similarity	NPD6898	Phase 1
0.6742	Remote Similarity	NPD7983	Approved
0.6742	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD6932	Approved
0.6629	Remote Similarity	NPD6698	Approved
0.6629	Remote Similarity	NPD46	Approved
0.6623	Remote Similarity	NPD6923	Approved
0.6623	Remote Similarity	NPD6922	Approved
0.6596	Remote Similarity	NPD6648	Approved
0.6585	Remote Similarity	NPD4271	Approved
0.6585	Remote Similarity	NPD4268	Approved
0.6571	Remote Similarity	NPD4219	Approved
0.6562	Remote Similarity	NPD4265	Approved
0.6538	Remote Similarity	NPD7144	Approved
0.6538	Remote Similarity	NPD7143	Approved
0.6526	Remote Similarity	NPD5344	Discontinued
0.6506	Remote Similarity	NPD6683	Phase 2
0.6506	Remote Similarity	NPD7645	Phase 2
0.6456	Remote Similarity	NPD7150	Approved
0.6456	Remote Similarity	NPD7152	Approved
0.6456	Remote Similarity	NPD7151	Approved
0.6438	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7525	Registered
0.6395	Remote Similarity	NPD5362	Discontinued
0.6374	Remote Similarity	NPD7637	Suspended
0.6333	Remote Similarity	NPD6101	Approved
0.6333	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4251	Approved
0.6292	Remote Similarity	NPD4250	Approved
0.6279	Remote Similarity	NPD6435	Approved
0.6277	Remote Similarity	NPD7839	Suspended
0.622	Remote Similarity	NPD7339	Approved
0.622	Remote Similarity	NPD6942	Approved
0.6207	Remote Similarity	NPD5331	Approved
0.6207	Remote Similarity	NPD5332	Approved
0.6196	Remote Similarity	NPD6411	Approved
0.619	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4249	Approved
0.6163	Remote Similarity	NPD4790	Discontinued
0.6145	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4270	Approved
0.6092	Remote Similarity	NPD4269	Approved
0.6087	Remote Similarity	NPD3168	Discontinued
0.6047	Remote Similarity	NPD5368	Approved
0.6026	Remote Similarity	NPD7331	Phase 2
0.6024	Remote Similarity	NPD8039	Approved
0.6	Remote Similarity	NPD5786	Approved
0.5977	Remote Similarity	NPD5369	Approved
0.5974	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7136	Phase 2
0.5897	Remote Similarity	NPD7341	Phase 2
0.5889	Remote Similarity	NPD1696	Phase 3
0.5889	Remote Similarity	NPD5363	Approved
0.5865	Remote Similarity	NPD6371	Approved
0.5862	Remote Similarity	NPD4252	Approved
0.5854	Remote Similarity	NPD4243	Approved
0.5844	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD5279	Phase 3
0.5816	Remote Similarity	NPD4225	Approved
0.5806	Remote Similarity	NPD1695	Approved
0.5797	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD1145	Discontinued
0.5784	Remote Similarity	NPD6640	Phase 3
0.5778	Remote Similarity	NPD4786	Approved
0.5758	Remote Similarity	NPD7640	Approved
0.5758	Remote Similarity	NPD7639	Approved
0.575	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD5785	Approved
0.573	Remote Similarity	NPD5209	Approved
0.573	Remote Similarity	NPD3667	Approved
0.5729	Remote Similarity	NPD5282	Discontinued
0.5714	Remote Similarity	NPD4191	Approved
0.5714	Remote Similarity	NPD4193	Approved
0.5714	Remote Similarity	NPD4194	Approved
0.5714	Remote Similarity	NPD4192	Approved
0.5714	Remote Similarity	NPD4785	Approved
0.5714	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4784	Approved
0.5682	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.567	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6110	Phase 1
0.566	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD7638	Approved
0.5638	Remote Similarity	NPD6051	Approved
0.5638	Remote Similarity	NPD5370	Suspended
0.5631	Remote Similarity	NPD5357	Phase 1
0.5625	Remote Similarity	NPD6399	Phase 3
0.5604	Remote Similarity	NPD3133	Approved
0.5604	Remote Similarity	NPD3666	Approved
0.5604	Remote Similarity	NPD3665	Phase 1

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