NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	338.25
Volume:	361.331
LogP:	3.151
LogD:	2.328
LogS:	-4.371
# Rotatable Bonds:	1
TPSA:	62.22
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.568
Synthetic Accessibility Score:	5.973
Fsp3:	0.9
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:	-4.699
MDCK Permeability:	1.682372203504201e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.067
30% Bioavailability (F30%):	0.137

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.477
Plasma Protein Binding (PPB):	88.73542785644531%
Volume Distribution (VD):	1.518
Pgp-substrate:	7.459205627441406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.327
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.212
CYP3A4-inhibitor:	0.349
CYP3A4-substrate:	0.42

ADMET: Excretion

Clearance (CL):	9.602
Half-life (T1/2):	0.569

ADMET: Toxicity

hERG Blockers:	0.091
Human Hepatotoxicity (H-HT):	0.795
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.181
Rat Oral Acute Toxicity:	0.391
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.779
Carcinogencity:	0.096
Eye Corrosion:	0.017
Eye Irritation:	0.19
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC476703

Natural Product ID:	NPC476703
*Common Name:**	Boscartin C
IUPAC Name:	(1S,3R,5R,7S,8E,12R,13R)-5,9,13-trimethyl-1-propan-2-yl-4,16-dioxatricyclo[11.2.1.03,5]hexadec-8-ene-7,12-diol
Synonyms:
Standard InCHIKey:	SMDIJQJOQYXYQB-ITZFYXQLSA-N
Standard InCHI:	InChI=1S/C20H34O4/c1-13(2)20-9-8-18(4,24-20)16(22)7-6-14(3)10-15(21)11-19(5)17(12-20)23-19/h10,13,15-17,21-22H,6-9,11-12H2,1-5H3/b14-10+/t15-,16-,17-,18-,19-,20+/m1/s1
SMILES:	C/C/1=C\[C@H](C[C@@]2([C@H](O2)C[C@@]3(CC[C@@](O3)([C@@H](CC1)O)C)C(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122196280
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 NPC476703 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	176
0.1-0.2	1536
0.2-0.3	5861
0.3-0.4	15783
0.4-0.5	9601
0.5-0.6	7160
0.6-0.7	2281
0.7-0.8	276
0.8-0.85	16
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9437	High Similarity	NPC476709
0.9054	High Similarity	NPC170148
0.9041	High Similarity	NPC190859
0.8947	High Similarity	NPC476701
0.8816	High Similarity	NPC477089
0.8493	Intermediate Similarity	NPC304690
0.8493	Intermediate Similarity	NPC329989
0.8493	Intermediate Similarity	NPC74722
0.8493	Intermediate Similarity	NPC239373
0.8493	Intermediate Similarity	NPC16964
0.8472	Intermediate Similarity	NPC259299
0.8378	Intermediate Similarity	NPC129630
0.8356	Intermediate Similarity	NPC305698
0.8353	Intermediate Similarity	NPC476705
0.8333	Intermediate Similarity	NPC68119
0.8333	Intermediate Similarity	NPC13823
0.8293	Intermediate Similarity	NPC298595
0.8289	Intermediate Similarity	NPC471525
0.8272	Intermediate Similarity	NPC231601
0.8243	Intermediate Similarity	NPC472947
0.8026	Intermediate Similarity	NPC306085
0.8025	Intermediate Similarity	NPC246621
0.8025	Intermediate Similarity	NPC474894
0.8	Intermediate Similarity	NPC476704
0.8	Intermediate Similarity	NPC476706
0.8	Intermediate Similarity	NPC476707
0.7975	Intermediate Similarity	NPC40049
0.7973	Intermediate Similarity	NPC163290
0.7973	Intermediate Similarity	NPC73603
0.7949	Intermediate Similarity	NPC12696
0.7945	Intermediate Similarity	NPC250836
0.7927	Intermediate Similarity	NPC477390
0.7927	Intermediate Similarity	NPC477385
0.7922	Intermediate Similarity	NPC329763
0.7875	Intermediate Similarity	NPC137345
0.7875	Intermediate Similarity	NPC3852
0.7875	Intermediate Similarity	NPC181838
0.7848	Intermediate Similarity	NPC268111
0.7848	Intermediate Similarity	NPC329626
0.7848	Intermediate Similarity	NPC293223
0.7848	Intermediate Similarity	NPC236228
0.7848	Intermediate Similarity	NPC256720
0.7838	Intermediate Similarity	NPC311736
0.7816	Intermediate Similarity	NPC191323
0.7765	Intermediate Similarity	NPC255143
0.775	Intermediate Similarity	NPC84360
0.7746	Intermediate Similarity	NPC475931
0.7722	Intermediate Similarity	NPC36479
0.7703	Intermediate Similarity	NPC471200
0.7701	Intermediate Similarity	NPC49783
0.7683	Intermediate Similarity	NPC474739
0.7674	Intermediate Similarity	NPC476948
0.7667	Intermediate Similarity	NPC14961
0.7667	Intermediate Similarity	NPC270013
0.7662	Intermediate Similarity	NPC470041
0.7654	Intermediate Similarity	NPC475980
0.764	Intermediate Similarity	NPC119379
0.7614	Intermediate Similarity	NPC197107
0.7614	Intermediate Similarity	NPC473448
0.7614	Intermediate Similarity	NPC3952
0.76	Intermediate Similarity	NPC267027
0.7586	Intermediate Similarity	NPC309656
0.7582	Intermediate Similarity	NPC476315
0.7582	Intermediate Similarity	NPC210717
0.7582	Intermediate Similarity	NPC103165
0.7568	Intermediate Similarity	NPC476702
0.7568	Intermediate Similarity	NPC300593
0.7561	Intermediate Similarity	NPC471537
0.7561	Intermediate Similarity	NPC86971
0.7558	Intermediate Similarity	NPC477389
0.7558	Intermediate Similarity	NPC477387
0.7558	Intermediate Similarity	NPC311163
0.7556	Intermediate Similarity	NPC81386
0.7556	Intermediate Similarity	NPC474035
0.7531	Intermediate Similarity	NPC477425
0.7531	Intermediate Similarity	NPC477427
0.7531	Intermediate Similarity	NPC474826
0.7531	Intermediate Similarity	NPC477426
0.7529	Intermediate Similarity	NPC78673
0.7529	Intermediate Similarity	NPC83702
0.7529	Intermediate Similarity	NPC160517
0.7529	Intermediate Similarity	NPC186155
0.7528	Intermediate Similarity	NPC302584
0.7528	Intermediate Similarity	NPC208839
0.75	Intermediate Similarity	NPC122239
0.75	Intermediate Similarity	NPC82337
0.75	Intermediate Similarity	NPC261807
0.75	Intermediate Similarity	NPC115607
0.75	Intermediate Similarity	NPC472465
0.75	Intermediate Similarity	NPC93213
0.75	Intermediate Similarity	NPC299527
0.75	Intermediate Similarity	NPC133450
0.75	Intermediate Similarity	NPC128066
0.7473	Intermediate Similarity	NPC36954
0.7473	Intermediate Similarity	NPC220221
0.7473	Intermediate Similarity	NPC476720
0.7471	Intermediate Similarity	NPC477388
0.7471	Intermediate Similarity	NPC477386
0.747	Intermediate Similarity	NPC472948
0.747	Intermediate Similarity	NPC100697
0.7468	Intermediate Similarity	NPC143576
0.7467	Intermediate Similarity	NPC473722
0.7465	Intermediate Similarity	NPC52012
0.7447	Intermediate Similarity	NPC476896
0.7444	Intermediate Similarity	NPC475912
0.7444	Intermediate Similarity	NPC212486
0.7442	Intermediate Similarity	NPC196911
0.7442	Intermediate Similarity	NPC471379
0.7432	Intermediate Similarity	NPC473508
0.7416	Intermediate Similarity	NPC472466
0.7416	Intermediate Similarity	NPC474761
0.7416	Intermediate Similarity	NPC177668
0.7416	Intermediate Similarity	NPC476004
0.7412	Intermediate Similarity	NPC320548
0.7407	Intermediate Similarity	NPC301525
0.7407	Intermediate Similarity	NPC126969
0.7403	Intermediate Similarity	NPC224532
0.7397	Intermediate Similarity	NPC258788
0.7391	Intermediate Similarity	NPC57664
0.7391	Intermediate Similarity	NPC279621
0.7386	Intermediate Similarity	NPC248312
0.7386	Intermediate Similarity	NPC231784
0.7381	Intermediate Similarity	NPC118116
0.7381	Intermediate Similarity	NPC77003
0.7375	Intermediate Similarity	NPC24590
0.7363	Intermediate Similarity	NPC473258
0.7361	Intermediate Similarity	NPC226848
0.7361	Intermediate Similarity	NPC181872
0.7356	Intermediate Similarity	NPC61527
0.7356	Intermediate Similarity	NPC247826
0.7356	Intermediate Similarity	NPC281316
0.7342	Intermediate Similarity	NPC471662
0.734	Intermediate Similarity	NPC272223
0.7333	Intermediate Similarity	NPC30515
0.7333	Intermediate Similarity	NPC184463
0.7333	Intermediate Similarity	NPC472468
0.7333	Intermediate Similarity	NPC309300
0.7333	Intermediate Similarity	NPC114389
0.7333	Intermediate Similarity	NPC158061
0.7317	Intermediate Similarity	NPC471454
0.7317	Intermediate Similarity	NPC476439
0.7312	Intermediate Similarity	NPC182811
0.7303	Intermediate Similarity	NPC97103
0.7303	Intermediate Similarity	NPC477917
0.7303	Intermediate Similarity	NPC473564
0.7303	Intermediate Similarity	NPC161560
0.7294	Intermediate Similarity	NPC155521
0.7283	Intermediate Similarity	NPC107476
0.7283	Intermediate Similarity	NPC240838
0.7273	Intermediate Similarity	NPC33583
0.7273	Intermediate Similarity	NPC472255
0.7273	Intermediate Similarity	NPC161612
0.7273	Intermediate Similarity	NPC472253
0.7273	Intermediate Similarity	NPC473357
0.7273	Intermediate Similarity	NPC474765
0.7273	Intermediate Similarity	NPC179659
0.7273	Intermediate Similarity	NPC193029
0.7262	Intermediate Similarity	NPC474592
0.7262	Intermediate Similarity	NPC95124
0.7262	Intermediate Similarity	NPC471266
0.7253	Intermediate Similarity	NPC98193
0.7253	Intermediate Similarity	NPC137461
0.7253	Intermediate Similarity	NPC228451
0.7253	Intermediate Similarity	NPC475838
0.7253	Intermediate Similarity	NPC476300
0.7253	Intermediate Similarity	NPC125674
0.725	Intermediate Similarity	NPC477085
0.7241	Intermediate Similarity	NPC471494
0.7241	Intermediate Similarity	NPC290731
0.7237	Intermediate Similarity	NPC61503
0.7237	Intermediate Similarity	NPC308844
0.7237	Intermediate Similarity	NPC19569
0.7234	Intermediate Similarity	NPC476895
0.7234	Intermediate Similarity	NPC274458
0.7222	Intermediate Similarity	NPC51004
0.7215	Intermediate Similarity	NPC471781
0.7215	Intermediate Similarity	NPC4299
0.7209	Intermediate Similarity	NPC185605
0.7209	Intermediate Similarity	NPC5958
0.7209	Intermediate Similarity	NPC260852
0.7209	Intermediate Similarity	NPC239308
0.7204	Intermediate Similarity	NPC90583
0.7204	Intermediate Similarity	NPC72204
0.7204	Intermediate Similarity	NPC288970
0.7195	Intermediate Similarity	NPC469880
0.7195	Intermediate Similarity	NPC271070
0.7191	Intermediate Similarity	NPC476708
0.7191	Intermediate Similarity	NPC228415
0.7191	Intermediate Similarity	NPC474668
0.7191	Intermediate Similarity	NPC87189
0.7188	Intermediate Similarity	NPC214714
0.7188	Intermediate Similarity	NPC200672
0.7188	Intermediate Similarity	NPC470972
0.7183	Intermediate Similarity	NPC223604
0.7183	Intermediate Similarity	NPC281590
0.7179	Intermediate Similarity	NPC167527
0.7179	Intermediate Similarity	NPC272961
0.7179	Intermediate Similarity	NPC470040
0.7176	Intermediate Similarity	NPC320525
0.7176	Intermediate Similarity	NPC471661

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 NPC476703 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	2186
0.2-0.3	3978
0.3-0.4	2056
0.4-0.5	506
0.5-0.6	193
0.6-0.7	62
0.7-0.8	4
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
0.7674	Intermediate Similarity	NPD7524	Approved
0.7529	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7838	Discovery
0.7412	Intermediate Similarity	NPD6695	Phase 3
0.7263	Intermediate Similarity	NPD5344	Discontinued
0.7222	Intermediate Similarity	NPD46	Approved
0.7222	Intermediate Similarity	NPD6698	Approved
0.7079	Intermediate Similarity	NPD7750	Discontinued
0.7067	Intermediate Similarity	NPD368	Approved
0.7059	Intermediate Similarity	NPD6931	Approved
0.7059	Intermediate Similarity	NPD6930	Phase 2
0.6957	Remote Similarity	NPD7983	Approved
0.6941	Remote Similarity	NPD6929	Approved
0.6889	Remote Similarity	NPD4251	Approved
0.6889	Remote Similarity	NPD4250	Approved
0.686	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4822	Approved
0.686	Remote Similarity	NPD4821	Approved
0.686	Remote Similarity	NPD4819	Approved
0.686	Remote Similarity	NPD4820	Approved
0.686	Remote Similarity	NPD7514	Phase 3
0.686	Remote Similarity	NPD7332	Phase 2
0.6804	Remote Similarity	NPD6648	Approved
0.6786	Remote Similarity	NPD6933	Approved
0.6782	Remote Similarity	NPD6902	Approved
0.6778	Remote Similarity	NPD4249	Approved
0.6774	Remote Similarity	NPD7087	Discontinued
0.6706	Remote Similarity	NPD5776	Phase 2
0.6706	Remote Similarity	NPD6925	Approved
0.6699	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD3168	Discontinued
0.6629	Remote Similarity	NPD7154	Phase 3
0.6628	Remote Similarity	NPD4268	Approved
0.6628	Remote Similarity	NPD7145	Approved
0.6628	Remote Similarity	NPD4271	Approved
0.6591	Remote Similarity	NPD6898	Phase 1
0.6569	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6926	Approved
0.6548	Remote Similarity	NPD6924	Approved
0.6531	Remote Similarity	NPD4225	Approved
0.6526	Remote Similarity	NPD5778	Approved
0.6526	Remote Similarity	NPD5779	Approved
0.6512	Remote Similarity	NPD6932	Approved
0.6486	Remote Similarity	NPD342	Phase 1
0.6484	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7525	Registered
0.6476	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5362	Discontinued
0.6444	Remote Similarity	NPD6110	Phase 1
0.6437	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7637	Suspended
0.6375	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6683	Phase 2
0.6346	Remote Similarity	NPD6686	Approved
0.6344	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6435	Approved
0.6311	Remote Similarity	NPD6640	Phase 3
0.6304	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7509	Discontinued
0.6289	Remote Similarity	NPD5282	Discontinued
0.6279	Remote Similarity	NPD8264	Approved
0.6264	Remote Similarity	NPD5332	Approved
0.6264	Remote Similarity	NPD5331	Approved
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4732	Discontinued
0.6234	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4790	Discontinued
0.6211	Remote Similarity	NPD1695	Approved
0.618	Remote Similarity	NPD7645	Phase 2
0.6154	Remote Similarity	NPD4270	Approved
0.6154	Remote Similarity	NPD5357	Phase 1
0.6154	Remote Similarity	NPD4269	Approved
0.6139	Remote Similarity	NPD7640	Approved
0.6139	Remote Similarity	NPD7639	Approved
0.6132	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5368	Approved
0.6095	Remote Similarity	NPD6412	Phase 2
0.6092	Remote Similarity	NPD6942	Approved
0.6092	Remote Similarity	NPD7339	Approved
0.6076	Remote Similarity	NPD1145	Discontinued
0.6071	Remote Similarity	NPD6923	Approved
0.6071	Remote Similarity	NPD6922	Approved
0.6064	Remote Similarity	NPD5786	Approved
0.6049	Remote Similarity	NPD371	Approved
0.6044	Remote Similarity	NPD5369	Approved
0.604	Remote Similarity	NPD7638	Approved
0.6036	Remote Similarity	NPD7115	Discovery
0.6023	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7144	Approved
0.6	Remote Similarity	NPD7839	Suspended
0.6	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7143	Approved
0.5982	Remote Similarity	NPD7328	Approved
0.5982	Remote Similarity	NPD7327	Approved
0.5979	Remote Similarity	NPD7136	Phase 2
0.5965	Remote Similarity	NPD8517	Approved
0.5965	Remote Similarity	NPD8513	Phase 3
0.5965	Remote Similarity	NPD8515	Approved
0.5965	Remote Similarity	NPD8516	Approved
0.5957	Remote Similarity	NPD5363	Approved
0.5934	Remote Similarity	NPD4252	Approved
0.593	Remote Similarity	NPD7152	Approved
0.593	Remote Similarity	NPD7151	Approved
0.593	Remote Similarity	NPD7150	Approved
0.5929	Remote Similarity	NPD7516	Approved
0.5922	Remote Similarity	NPD4159	Approved
0.5915	Remote Similarity	NPD4265	Approved
0.59	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD8294	Approved
0.5877	Remote Similarity	NPD8377	Approved
0.5876	Remote Similarity	NPD6101	Approved
0.5876	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD8379	Approved
0.5826	Remote Similarity	NPD8380	Approved
0.5826	Remote Similarity	NPD8033	Approved
0.5826	Remote Similarity	NPD8378	Approved
0.5826	Remote Similarity	NPD8296	Approved
0.5826	Remote Similarity	NPD7503	Approved
0.5826	Remote Similarity	NPD8335	Approved
0.5818	Remote Similarity	NPD6053	Discontinued
0.5816	Remote Similarity	NPD5785	Approved
0.5816	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.578	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD8273	Phase 1
0.5758	Remote Similarity	NPD6411	Approved
0.5747	Remote Similarity	NPD4243	Approved
0.5714	Remote Similarity	NPD8074	Phase 3
0.5714	Remote Similarity	NPD6051	Approved
0.57	Remote Similarity	NPD6399	Phase 3
0.5684	Remote Similarity	NPD4786	Approved
0.5648	Remote Similarity	NPD6685	Approved
0.5638	Remote Similarity	NPD3667	Approved
0.5638	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD6083	Phase 2
0.5631	Remote Similarity	NPD6084	Phase 2
0.563	Remote Similarity	NPD7507	Approved
0.5618	Remote Similarity	NPD4784	Approved
0.5618	Remote Similarity	NPD4785	Approved
0.5614	Remote Similarity	NPD7505	Discontinued
0.5603	Remote Similarity	NPD6054	Approved
0.5603	Remote Similarity	NPD6059	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