NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	322.25
Volume:	352.541
LogP:	4.005
LogD:	3.349
LogS:	-4.941
# Rotatable Bonds:	1
TPSA:	41.99
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.575
Synthetic Accessibility Score:	5.73
Fsp3:	0.9
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:	-4.655
MDCK Permeability:	2.7901478460989892e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.056
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.048

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.217
Plasma Protein Binding (PPB):	94.4765853881836%
Volume Distribution (VD):	1.389
Pgp-substrate:	3.2825117111206055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.268
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.353
CYP3A4-inhibitor:	0.397
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	8.917
Half-life (T1/2):	0.436

ADMET: Toxicity

hERG Blockers:	0.177
Human Hepatotoxicity (H-HT):	0.658
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.925
Carcinogencity:	0.064
Eye Corrosion:	0.193
Eye Irritation:	0.578
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC476709

Natural Product ID:	NPC476709
*Common Name:**	(1R,3S,6R,10E,14R)-3-Isopropyl-6,10,14-trimethyl-1,14:3,6-diepoxycyclotetradeca-10-ene-7alpha-ol
IUPAC Name:	(1S,3R,5R,8E,12R,13R)-5,9,13-trimethyl-1-propan-2-yl-4,16-dioxatricyclo[11.2.1.03,5]hexadec-8-en-12-ol
Synonyms:
Standard InCHIKey:	ARTVDMKLQDTMGX-RHKYAHEOSA-N
Standard InCHI:	InChI=1S/C20H34O3/c1-14(2)20-12-11-18(4,23-20)16(21)9-8-15(3)7-6-10-19(5)17(13-20)22-19/h7,14,16-17,21H,6,8-13H2,1-5H3/b15-7+/t16-,17-,18-,19-,20+/m1/s1
SMILES:	C/C/1=C\CC[C@@]2([C@H](O2)C[C@@]3(CC[C@@](O3)([C@@H](CC1)O)C)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122196279
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
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24195447]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	Gum resin	n.a.	n.a.	PMID[26457560]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15315	Boswellia carterii	Species	Burseraceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Survival	=	87	%	PMID[26457560]

☑ 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 NPC476709 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	179
0.1-0.2	1662
0.2-0.3	7605
0.3-0.4	15924
0.4-0.5	8195
0.5-0.6	7298
0.6-0.7	1668
0.7-0.8	154
0.8-0.85	9
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9437	High Similarity	NPC476703
0.8784	High Similarity	NPC477089
0.875	High Similarity	NPC190859
0.8714	High Similarity	NPC16964
0.8667	High Similarity	NPC476701
0.8514	High Similarity	NPC170148
0.8378	Intermediate Similarity	NPC12696
0.8243	Intermediate Similarity	NPC471525
0.8219	Intermediate Similarity	NPC306085
0.8194	Intermediate Similarity	NPC239373
0.8194	Intermediate Similarity	NPC304690
0.8194	Intermediate Similarity	NPC329989
0.8194	Intermediate Similarity	NPC74722
0.8171	Intermediate Similarity	NPC476707
0.8171	Intermediate Similarity	NPC476704
0.8171	Intermediate Similarity	NPC476706
0.8169	Intermediate Similarity	NPC259299
0.8143	Intermediate Similarity	NPC471200
0.8082	Intermediate Similarity	NPC470041
0.8082	Intermediate Similarity	NPC129630
0.8056	Intermediate Similarity	NPC305698
0.8052	Intermediate Similarity	NPC3852
0.8026	Intermediate Similarity	NPC293223
0.8	Intermediate Similarity	NPC231601
0.7945	Intermediate Similarity	NPC472947
0.7895	Intermediate Similarity	NPC36479
0.7882	Intermediate Similarity	NPC476705
0.7821	Intermediate Similarity	NPC68119
0.7821	Intermediate Similarity	NPC13823
0.7805	Intermediate Similarity	NPC298595
0.7792	Intermediate Similarity	NPC329626
0.775	Intermediate Similarity	NPC246621
0.775	Intermediate Similarity	NPC474894
0.7746	Intermediate Similarity	NPC476702
0.7738	Intermediate Similarity	NPC309656
0.7671	Intermediate Similarity	NPC472253
0.7671	Intermediate Similarity	NPC33583
0.7671	Intermediate Similarity	NPC472255
0.7671	Intermediate Similarity	NPC161612
0.7662	Intermediate Similarity	NPC93213
0.7647	Intermediate Similarity	NPC52012
0.7639	Intermediate Similarity	NPC250836
0.7639	Intermediate Similarity	NPC61503
0.7632	Intermediate Similarity	NPC329763
0.7625	Intermediate Similarity	NPC100697
0.7625	Intermediate Similarity	NPC472948
0.7612	Intermediate Similarity	NPC223604
0.76	Intermediate Similarity	NPC471781
0.7568	Intermediate Similarity	NPC470040
0.7564	Intermediate Similarity	NPC256720
0.7564	Intermediate Similarity	NPC236228
0.7564	Intermediate Similarity	NPC268111
0.7534	Intermediate Similarity	NPC272125
0.7534	Intermediate Similarity	NPC311736
0.7531	Intermediate Similarity	NPC118116
0.75	Intermediate Similarity	NPC287744
0.75	Intermediate Similarity	NPC125399
0.75	Intermediate Similarity	NPC255143
0.75	Intermediate Similarity	NPC247826
0.75	Intermediate Similarity	NPC140233
0.7468	Intermediate Similarity	NPC40049
0.7467	Intermediate Similarity	NPC329656
0.7439	Intermediate Similarity	NPC477390
0.7439	Intermediate Similarity	NPC477385
0.7432	Intermediate Similarity	NPC163290
0.7432	Intermediate Similarity	NPC473357
0.7432	Intermediate Similarity	NPC73603
0.7432	Intermediate Similarity	NPC193029
0.7429	Intermediate Similarity	NPC475931
0.7412	Intermediate Similarity	NPC476948
0.7407	Intermediate Similarity	NPC474739
0.7403	Intermediate Similarity	NPC143576
0.7386	Intermediate Similarity	NPC98193
0.7386	Intermediate Similarity	NPC212486
0.7386	Intermediate Similarity	NPC119379
0.7381	Intermediate Similarity	NPC290731
0.7375	Intermediate Similarity	NPC181838
0.7375	Intermediate Similarity	NPC137345
0.7361	Intermediate Similarity	NPC50435
0.7356	Intermediate Similarity	NPC191323
0.7353	Intermediate Similarity	NPC281590
0.7349	Intermediate Similarity	NPC239308
0.7333	Intermediate Similarity	NPC103165
0.7333	Intermediate Similarity	NPC210717
0.7326	Intermediate Similarity	NPC476708
0.7297	Intermediate Similarity	NPC267027
0.7297	Intermediate Similarity	NPC469328
0.7273	Intermediate Similarity	NPC208839
0.7273	Intermediate Similarity	NPC210268
0.7273	Intermediate Similarity	NPC41886
0.7273	Intermediate Similarity	NPC184463
0.726	Intermediate Similarity	NPC309300
0.726	Intermediate Similarity	NPC300593
0.7253	Intermediate Similarity	NPC261807
0.725	Intermediate Similarity	NPC130136
0.725	Intermediate Similarity	NPC84360
0.725	Intermediate Similarity	NPC477426
0.725	Intermediate Similarity	NPC477425
0.725	Intermediate Similarity	NPC471454
0.725	Intermediate Similarity	NPC186109
0.725	Intermediate Similarity	NPC477427
0.725	Intermediate Similarity	NPC474826
0.7241	Intermediate Similarity	NPC133450
0.7241	Intermediate Similarity	NPC473058
0.7241	Intermediate Similarity	NPC49783
0.7237	Intermediate Similarity	NPC144647
0.7229	Intermediate Similarity	NPC20072
0.7222	Intermediate Similarity	NPC270013
0.7222	Intermediate Similarity	NPC64971
0.7222	Intermediate Similarity	NPC14961
0.7222	Intermediate Similarity	NPC475251
0.7222	Intermediate Similarity	NPC63111
0.7215	Intermediate Similarity	NPC113639
0.7209	Intermediate Similarity	NPC189777
0.72	Intermediate Similarity	NPC82337
0.7195	Intermediate Similarity	NPC103634
0.7195	Intermediate Similarity	NPC474592
0.7183	Intermediate Similarity	NPC122239
0.7176	Intermediate Similarity	NPC471379
0.7176	Intermediate Similarity	NPC474189
0.7176	Intermediate Similarity	NPC474349
0.7176	Intermediate Similarity	NPC196911
0.7162	Intermediate Similarity	NPC477009
0.7162	Intermediate Similarity	NPC473722
0.7162	Intermediate Similarity	NPC238352
0.716	Intermediate Similarity	NPC475980
0.716	Intermediate Similarity	NPC11796
0.716	Intermediate Similarity	NPC218817
0.716	Intermediate Similarity	NPC52755
0.7159	Intermediate Similarity	NPC197107
0.7159	Intermediate Similarity	NPC473448
0.7159	Intermediate Similarity	NPC3952
0.7159	Intermediate Similarity	NPC470832
0.7159	Intermediate Similarity	NPC177668
0.7159	Intermediate Similarity	NPC159876
0.7143	Intermediate Similarity	NPC320548
0.7143	Intermediate Similarity	NPC260852
0.7143	Intermediate Similarity	NPC476315
0.7126	Intermediate Similarity	NPC248312
0.7125	Intermediate Similarity	NPC126969
0.7125	Intermediate Similarity	NPC301525
0.7125	Intermediate Similarity	NPC315261
0.7123	Intermediate Similarity	NPC279200
0.7123	Intermediate Similarity	NPC473508
0.7111	Intermediate Similarity	NPC81386
0.7111	Intermediate Similarity	NPC174051
0.7111	Intermediate Similarity	NPC474035
0.7111	Intermediate Similarity	NPC67831
0.7108	Intermediate Similarity	NPC77003
0.7108	Intermediate Similarity	NPC207188
0.7105	Intermediate Similarity	NPC224532
0.7105	Intermediate Similarity	NPC272961
0.7097	Intermediate Similarity	NPC324598
0.7093	Intermediate Similarity	NPC477387
0.7093	Intermediate Similarity	NPC476217
0.7093	Intermediate Similarity	NPC470836
0.7093	Intermediate Similarity	NPC477389
0.7093	Intermediate Similarity	NPC311163
0.7093	Intermediate Similarity	NPC281316
0.7079	Intermediate Similarity	NPC114389
0.7079	Intermediate Similarity	NPC30515
0.7079	Intermediate Similarity	NPC262870
0.7079	Intermediate Similarity	NPC302584
0.7073	Intermediate Similarity	NPC86971
0.7073	Intermediate Similarity	NPC471537
0.7073	Intermediate Similarity	NPC233295
0.7065	Intermediate Similarity	NPC476021
0.7065	Intermediate Similarity	NPC476040
0.7065	Intermediate Similarity	NPC474994
0.7059	Intermediate Similarity	NPC186155
0.7059	Intermediate Similarity	NPC166279
0.7059	Intermediate Similarity	NPC160517
0.7059	Intermediate Similarity	NPC319238
0.7059	Intermediate Similarity	NPC78673
0.7059	Intermediate Similarity	NPC83702
0.7051	Intermediate Similarity	NPC471662
0.7045	Intermediate Similarity	NPC128066
0.7045	Intermediate Similarity	NPC161560
0.7045	Intermediate Similarity	NPC97103
0.7045	Intermediate Similarity	NPC299527
0.7045	Intermediate Similarity	NPC115607
0.7045	Intermediate Similarity	NPC307411
0.7045	Intermediate Similarity	NPC473564
0.7042	Intermediate Similarity	NPC226848
0.7042	Intermediate Similarity	NPC181872
0.7042	Intermediate Similarity	NPC41180
0.7042	Intermediate Similarity	NPC152438
0.7037	Intermediate Similarity	NPC31037
0.7037	Intermediate Similarity	NPC476439
0.7033	Intermediate Similarity	NPC36954
0.7033	Intermediate Similarity	NPC240838
0.7033	Intermediate Similarity	NPC220221
0.7033	Intermediate Similarity	NPC476720
0.7033	Intermediate Similarity	NPC8774
0.7033	Intermediate Similarity	NPC107476
0.7027	Intermediate Similarity	NPC225415
0.7027	Intermediate Similarity	NPC199937
0.7024	Intermediate Similarity	NPC103171
0.7024	Intermediate Similarity	NPC155521
0.7024	Intermediate Similarity	NPC472465

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 NPC476709 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	2451
0.2-0.3	4061
0.3-0.4	1789
0.4-0.5	415
0.5-0.6	216
0.6-0.7	48
0.7-0.8	1
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
0.7412	Intermediate Similarity	NPD7524	Approved
0.7262	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7838	Discovery
0.7143	Intermediate Similarity	NPD6695	Phase 3
0.7125	Intermediate Similarity	NPD6933	Approved
0.6988	Remote Similarity	NPD6930	Phase 2
0.6988	Remote Similarity	NPD6931	Approved
0.6966	Remote Similarity	NPD6698	Approved
0.6966	Remote Similarity	NPD46	Approved
0.6875	Remote Similarity	NPD6926	Approved
0.6875	Remote Similarity	NPD6924	Approved
0.6867	Remote Similarity	NPD6929	Approved
0.6842	Remote Similarity	NPD5344	Discontinued
0.6829	Remote Similarity	NPD6932	Approved
0.6818	Remote Similarity	NPD7750	Discontinued
0.6778	Remote Similarity	NPD3168	Discontinued
0.6757	Remote Similarity	NPD368	Approved
0.6667	Remote Similarity	NPD6683	Phase 2
0.6627	Remote Similarity	NPD6925	Approved
0.6627	Remote Similarity	NPD5776	Phase 2
0.6591	Remote Similarity	NPD6893	Approved
0.6588	Remote Similarity	NPD7509	Discontinued
0.6588	Remote Similarity	NPD7514	Phase 3
0.6588	Remote Similarity	NPD7332	Phase 2
0.6588	Remote Similarity	NPD7525	Registered
0.6548	Remote Similarity	NPD7145	Approved
0.6522	Remote Similarity	NPD7983	Approved
0.6522	Remote Similarity	NPD7087	Discontinued
0.6512	Remote Similarity	NPD6902	Approved
0.6512	Remote Similarity	NPD6898	Phase 1
0.6471	Remote Similarity	NPD7645	Phase 2
0.6444	Remote Similarity	NPD4251	Approved
0.6444	Remote Similarity	NPD4250	Approved
0.6437	Remote Similarity	NPD6435	Approved
0.6404	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1145	Discontinued
0.6395	Remote Similarity	NPD4820	Approved
0.6395	Remote Similarity	NPD4819	Approved
0.6395	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4822	Approved
0.6395	Remote Similarity	NPD4821	Approved
0.6392	Remote Similarity	NPD6648	Approved
0.6386	Remote Similarity	NPD7339	Approved
0.6386	Remote Similarity	NPD6942	Approved
0.6383	Remote Similarity	NPD5282	Discontinued
0.6375	Remote Similarity	NPD6923	Approved
0.6375	Remote Similarity	NPD6922	Approved
0.6364	Remote Similarity	NPD371	Approved
0.6337	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4249	Approved
0.6311	Remote Similarity	NPD6371	Approved
0.631	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD1695	Approved
0.6296	Remote Similarity	NPD7143	Approved
0.6296	Remote Similarity	NPD7144	Approved
0.6282	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5357	Phase 1
0.6222	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7151	Approved
0.622	Remote Similarity	NPD7150	Approved
0.622	Remote Similarity	NPD7152	Approved
0.6207	Remote Similarity	NPD5368	Approved
0.618	Remote Similarity	NPD7154	Phase 3
0.6176	Remote Similarity	NPD6412	Phase 2
0.6164	Remote Similarity	NPD342	Phase 1
0.6163	Remote Similarity	NPD4271	Approved
0.6163	Remote Similarity	NPD4268	Approved
0.6163	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5369	Approved
0.6122	Remote Similarity	NPD4225	Approved
0.6117	Remote Similarity	NPD6686	Approved
0.6105	Remote Similarity	NPD5779	Approved
0.6105	Remote Similarity	NPD5778	Approved
0.61	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD4243	Approved
0.6	Remote Similarity	NPD5362	Discontinued
0.6	Remote Similarity	NPD6110	Phase 1
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD8264	Approved
0.596	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6101	Approved
0.5957	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD4732	Discontinued
0.5934	Remote Similarity	NPD4786	Approved
0.5922	Remote Similarity	NPD6640	Phase 3
0.5905	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD3667	Approved
0.5882	Remote Similarity	NPD4785	Approved
0.5882	Remote Similarity	NPD4784	Approved
0.5842	Remote Similarity	NPD4159	Approved
0.5833	Remote Similarity	NPD6411	Approved
0.5824	Remote Similarity	NPD5332	Approved
0.5824	Remote Similarity	NPD5331	Approved
0.5816	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD7331	Phase 2
0.58	Remote Similarity	NPD7638	Approved
0.5795	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD4790	Discontinued
0.5773	Remote Similarity	NPD6399	Phase 3
0.5766	Remote Similarity	NPD7328	Approved
0.5766	Remote Similarity	NPD7327	Approved
0.5761	Remote Similarity	NPD3133	Approved
0.5761	Remote Similarity	NPD3666	Approved
0.5761	Remote Similarity	NPD3665	Phase 1
0.575	Remote Similarity	NPD3197	Phase 1
0.5743	Remote Similarity	NPD7640	Approved
0.5743	Remote Similarity	NPD7639	Approved
0.5729	Remote Similarity	NPD7136	Phase 2
0.5714	Remote Similarity	NPD7516	Approved
0.5714	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6685	Approved
0.5714	Remote Similarity	NPD4269	Approved
0.5714	Remote Similarity	NPD4270	Approved
0.57	Remote Similarity	NPD6084	Phase 2
0.57	Remote Similarity	NPD6083	Phase 2
0.5679	Remote Similarity	NPD7341	Phase 2
0.5676	Remote Similarity	NPD7115	Discovery
0.5667	Remote Similarity	NPD4748	Discontinued
0.5664	Remote Similarity	NPD6059	Approved
0.5664	Remote Similarity	NPD8294	Approved
0.5664	Remote Similarity	NPD6054	Approved
0.5664	Remote Similarity	NPD8377	Approved
0.5638	Remote Similarity	NPD3618	Phase 1
0.5638	Remote Similarity	NPD5279	Phase 3
0.5638	Remote Similarity	NPD5786	Approved
0.5632	Remote Similarity	NPD4190	Phase 3
0.5632	Remote Similarity	NPD5275	Approved
0.5625	Remote Similarity	NPD5328	Approved
0.5625	Remote Similarity	NPD4753	Phase 2
0.5619	Remote Similarity	NPD5739	Approved
0.5619	Remote Similarity	NPD6402	Approved
0.5619	Remote Similarity	NPD7128	Approved
0.5619	Remote Similarity	NPD6675	Approved
0.5614	Remote Similarity	NPD8516	Approved
0.5614	Remote Similarity	NPD8517	Approved
0.5614	Remote Similarity	NPD8378	Approved
0.5614	Remote Similarity	NPD8380	Approved
0.5614	Remote Similarity	NPD8296	Approved
0.5614	Remote Similarity	NPD8513	Phase 3
0.5614	Remote Similarity	NPD8379	Approved
0.5614	Remote Similarity	NPD7503	Approved
0.5614	Remote Similarity	NPD8515	Approved
0.5614	Remote Similarity	NPD8033	Approved
0.5614	Remote Similarity	NPD8335	Approved
0.5612	Remote Similarity	NPD4202	Approved
0.56	Remote Similarity	NPD7839	Suspended
0.56	Remote Similarity	NPD4792	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