NPASS Compound

Structure

NPC471661 OpenBabel07101719252D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.0283 -3.5132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1276 0.5837 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5311 -2.7219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1490 -1.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0915 -1.8359 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4148 -0.8895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5283 -2.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0917 -1.8209 0.0000 C 0 0 1 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 -0.0000 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7969 -0.8653 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6146 -0.2897 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1275 0.5687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 6 24 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 12 1 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 14 9 1 6 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 6 0 0 0 16 21 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 6 0 0 0 18 21 1 6 0 0 0 19 22 1 0 0 0 0 20 4 1 1 0 0 0 20 23 1 0 0 0 0 21 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.25
Volume:	367.201
LogP:	3.3
LogD:	3.339
LogS:	-4.066
# Rotatable Bonds:	4
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.771
Synthetic Accessibility Score:	5.185
Fsp3:	0.81
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:	-4.428
MDCK Permeability:	2.2439795429818332e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.074
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.933
Plasma Protein Binding (PPB):	77.51116180419922%
Volume Distribution (VD):	0.819
Pgp-substrate:	13.80054759979248%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.302
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.13
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.466
CYP3A4-inhibitor:	0.449
CYP3A4-substrate:	0.441

ADMET: Excretion

Clearance (CL):	6.685
Half-life (T1/2):	0.565

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.294
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.211
Maximum Recommended Daily Dose:	0.73
Skin Sensitization:	0.041
Carcinogencity:	0.026
Eye Corrosion:	0.007
Eye Irritation:	0.051
Respiratory Toxicity:	0.675

Download Data

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

Natural Product: NPC471661

Natural Product ID:	NPC471661
*Common Name:**	Boscarterol D
IUPAC Name:	(1S,1aR,4aR,7S,7aS,7bR)-1-[(E)-4-hydroxy-1-methoxy-4-methylpent-2-enyl]-1,7-dimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-ol
Synonyms:
Standard InCHIKey:	UEGIIVCBJXWWFP-WOMSTJCLSA-N
Standard InCHI:	InChI=1S/C21H34O3/c1-13-7-8-15-18(17-14(13)9-12-20(17,4)23)21(15,5)16(24-6)10-11-19(2,3)22/h10-11,14-18,22-23H,1,7-9,12H2,2-6H3/b11-10+/t14-,15+,16?,17-,18+,20-,21+/m0/s1
SMILES:	COC([C@@]1(C)[C@H]2[C@@H]1[C@@H]1[C@H](C(=C)CC2)CC[C@]1(C)O)/C=C/C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3087765
PubChem CID:	76328042
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003550] Pachydictyane and cneorubin diterpenoids

*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
IC50	5

Activity Type	# Activity
Cell Line	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[494330]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[494330]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[494330]

☑ 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 NPC471661 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	200
0.1-0.2	1805
0.2-0.3	8475
0.3-0.4	16194
0.4-0.5	8458
0.5-0.6	6024
0.6-0.7	1423
0.7-0.8	108
0.8-0.85	5
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8816	High Similarity	NPC471659
0.88	High Similarity	NPC471660
0.859	High Similarity	NPC471658
0.8553	High Similarity	NPC471662
0.8481	Intermediate Similarity	NPC471454
0.8125	Intermediate Similarity	NPC126969
0.8125	Intermediate Similarity	NPC310643
0.8095	Intermediate Similarity	NPC471340
0.7976	Intermediate Similarity	NPC472465
0.7931	Intermediate Similarity	NPC45957
0.7931	Intermediate Similarity	NPC471657
0.7922	Intermediate Similarity	NPC224532
0.7821	Intermediate Similarity	NPC144647
0.7805	Intermediate Similarity	NPC476439
0.7802	Intermediate Similarity	NPC472467
0.7792	Intermediate Similarity	NPC136813
0.7763	Intermediate Similarity	NPC477009
0.7763	Intermediate Similarity	NPC238352
0.7733	Intermediate Similarity	NPC474480
0.7692	Intermediate Similarity	NPC167527
0.7683	Intermediate Similarity	NPC476317
0.7667	Intermediate Similarity	NPC295668
0.7647	Intermediate Similarity	NPC472471
0.7632	Intermediate Similarity	NPC309300
0.7625	Intermediate Similarity	NPC41886
0.7614	Intermediate Similarity	NPC137253
0.7595	Intermediate Similarity	NPC74722
0.7595	Intermediate Similarity	NPC304690
0.759	Intermediate Similarity	NPC186109
0.7582	Intermediate Similarity	NPC472468
0.7564	Intermediate Similarity	NPC477791
0.7564	Intermediate Similarity	NPC259299
0.7532	Intermediate Similarity	NPC19569
0.7531	Intermediate Similarity	NPC234527
0.7531	Intermediate Similarity	NPC14352
0.7529	Intermediate Similarity	NPC471656
0.75	Intermediate Similarity	NPC470041
0.75	Intermediate Similarity	NPC274448
0.75	Intermediate Similarity	NPC254845
0.7473	Intermediate Similarity	NPC472466
0.7471	Intermediate Similarity	NPC477667
0.7471	Intermediate Similarity	NPC472473
0.747	Intermediate Similarity	NPC268111
0.7468	Intermediate Similarity	NPC305698
0.7467	Intermediate Similarity	NPC252809
0.7467	Intermediate Similarity	NPC323153
0.7439	Intermediate Similarity	NPC309178
0.7419	Intermediate Similarity	NPC144202
0.7419	Intermediate Similarity	NPC473258
0.7419	Intermediate Similarity	NPC281775
0.7416	Intermediate Similarity	NPC477668
0.7416	Intermediate Similarity	NPC152808
0.7416	Intermediate Similarity	NPC293287
0.7403	Intermediate Similarity	NPC140233
0.7403	Intermediate Similarity	NPC287744
0.7391	Intermediate Similarity	NPC249034
0.7386	Intermediate Similarity	NPC116613
0.7386	Intermediate Similarity	NPC470077
0.7381	Intermediate Similarity	NPC31037
0.7368	Intermediate Similarity	NPC210346
0.7368	Intermediate Similarity	NPC63111
0.7363	Intermediate Similarity	NPC170775
0.7356	Intermediate Similarity	NPC50964
0.7349	Intermediate Similarity	NPC113639
0.7349	Intermediate Similarity	NPC60818
0.7349	Intermediate Similarity	NPC313185
0.7349	Intermediate Similarity	NPC23231
0.7342	Intermediate Similarity	NPC472253
0.7342	Intermediate Similarity	NPC472255
0.7333	Intermediate Similarity	NPC149224
0.7333	Intermediate Similarity	NPC99480
0.7333	Intermediate Similarity	NPC184049
0.7333	Intermediate Similarity	NPC5698
0.7326	Intermediate Similarity	NPC324772
0.7317	Intermediate Similarity	NPC329763
0.7312	Intermediate Similarity	NPC27531
0.7308	Intermediate Similarity	NPC205618
0.7308	Intermediate Similarity	NPC469326
0.7308	Intermediate Similarity	NPC261782
0.7303	Intermediate Similarity	NPC157257
0.7294	Intermediate Similarity	NPC477089
0.7284	Intermediate Similarity	NPC471781
0.7283	Intermediate Similarity	NPC197107
0.7283	Intermediate Similarity	NPC209816
0.7273	Intermediate Similarity	NPC470558
0.7273	Intermediate Similarity	NPC475789
0.7273	Intermediate Similarity	NPC82623
0.7253	Intermediate Similarity	NPC471952
0.7241	Intermediate Similarity	NPC82986
0.7241	Intermediate Similarity	NPC320525
0.7241	Intermediate Similarity	NPC474759
0.7241	Intermediate Similarity	NPC7505
0.7241	Intermediate Similarity	NPC474752
0.7241	Intermediate Similarity	NPC264245
0.7241	Intermediate Similarity	NPC209620
0.7241	Intermediate Similarity	NPC474683
0.7241	Intermediate Similarity	NPC474731
0.7241	Intermediate Similarity	NPC23852
0.7222	Intermediate Similarity	NPC261266
0.7222	Intermediate Similarity	NPC139724
0.7216	Intermediate Similarity	NPC130792
0.7215	Intermediate Similarity	NPC272125
0.7215	Intermediate Similarity	NPC469328
0.7209	Intermediate Similarity	NPC325869
0.72	Intermediate Similarity	NPC179891
0.7195	Intermediate Similarity	NPC469343
0.7191	Intermediate Similarity	NPC16887
0.7191	Intermediate Similarity	NPC53011
0.7191	Intermediate Similarity	NPC37005
0.7191	Intermediate Similarity	NPC154893
0.7191	Intermediate Similarity	NPC222634
0.7191	Intermediate Similarity	NPC474047
0.7188	Intermediate Similarity	NPC477949
0.7176	Intermediate Similarity	NPC84360
0.7176	Intermediate Similarity	NPC476703
0.7174	Intermediate Similarity	NPC299527
0.716	Intermediate Similarity	NPC22301
0.7159	Intermediate Similarity	NPC470049
0.7159	Intermediate Similarity	NPC218616
0.7159	Intermediate Similarity	NPC296701
0.7159	Intermediate Similarity	NPC49964
0.7159	Intermediate Similarity	NPC87489
0.7143	Intermediate Similarity	NPC471796
0.7128	Intermediate Similarity	NPC37816
0.7126	Intermediate Similarity	NPC241290
0.7126	Intermediate Similarity	NPC474592
0.7126	Intermediate Similarity	NPC26117
0.7126	Intermediate Similarity	NPC186072
0.7126	Intermediate Similarity	NPC209944
0.7126	Intermediate Similarity	NPC234193
0.7126	Intermediate Similarity	NPC164840
0.7126	Intermediate Similarity	NPC472470
0.7125	Intermediate Similarity	NPC73603
0.7113	Intermediate Similarity	NPC109556
0.7111	Intermediate Similarity	NPC318390
0.7111	Intermediate Similarity	NPC470360
0.7111	Intermediate Similarity	NPC146850
0.7111	Intermediate Similarity	NPC266511
0.7111	Intermediate Similarity	NPC287015
0.7105	Intermediate Similarity	NPC52431
0.7105	Intermediate Similarity	NPC310228
0.7097	Intermediate Similarity	NPC37607
0.7097	Intermediate Similarity	NPC301969
0.7097	Intermediate Similarity	NPC470832
0.7093	Intermediate Similarity	NPC470944
0.7093	Intermediate Similarity	NPC477514
0.7089	Intermediate Similarity	NPC61503
0.7087	Intermediate Similarity	NPC15551
0.7083	Intermediate Similarity	NPC288970
0.7083	Intermediate Similarity	NPC72204
0.7083	Intermediate Similarity	NPC113433
0.7079	Intermediate Similarity	NPC477818
0.7079	Intermediate Similarity	NPC320548
0.7079	Intermediate Similarity	NPC134481
0.7065	Intermediate Similarity	NPC133588
0.7059	Intermediate Similarity	NPC247325
0.7059	Intermediate Similarity	NPC244488
0.7059	Intermediate Similarity	NPC308191
0.7059	Intermediate Similarity	NPC256720
0.7059	Intermediate Similarity	NPC236228
0.7059	Intermediate Similarity	NPC152017
0.7053	Intermediate Similarity	NPC65402
0.7053	Intermediate Similarity	NPC127718
0.7051	Intermediate Similarity	NPC279200
0.7045	Intermediate Similarity	NPC47761
0.7041	Intermediate Similarity	NPC290802
0.7033	Intermediate Similarity	NPC299068
0.7033	Intermediate Similarity	NPC474045
0.7033	Intermediate Similarity	NPC6391
0.7033	Intermediate Similarity	NPC261253
0.7024	Intermediate Similarity	NPC306727
0.7024	Intermediate Similarity	NPC329090
0.7024	Intermediate Similarity	NPC27395
0.7021	Intermediate Similarity	NPC275671
0.7021	Intermediate Similarity	NPC234335
0.7019	Intermediate Similarity	NPC71680
0.7011	Intermediate Similarity	NPC226226
0.7011	Intermediate Similarity	NPC28862
0.7011	Intermediate Similarity	NPC204270
0.7011	Intermediate Similarity	NPC55304
0.7011	Intermediate Similarity	NPC47982
0.7011	Intermediate Similarity	NPC109546
0.7011	Intermediate Similarity	NPC84694
0.7011	Intermediate Similarity	NPC476701
0.7011	Intermediate Similarity	NPC30986
0.7011	Intermediate Similarity	NPC233295
0.7011	Intermediate Similarity	NPC81306
0.7011	Intermediate Similarity	NPC209430
0.7011	Intermediate Similarity	NPC143182
0.701	Intermediate Similarity	NPC261807
0.701	Intermediate Similarity	NPC182811
0.7	Intermediate Similarity	NPC83702
0.7	Intermediate Similarity	NPC78673
0.7	Intermediate Similarity	NPC238485
0.7	Intermediate Similarity	NPC231310
0.7	Intermediate Similarity	NPC160517
0.7	Intermediate Similarity	NPC162309
0.7	Intermediate Similarity	NPC186155
0.7	Intermediate Similarity	NPC205845
0.699	Remote Similarity	NPC475274

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 NPC471661 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	2390
0.2-0.3	4262
0.3-0.4	1729
0.4-0.5	325
0.5-0.6	202
0.6-0.7	53
0.7-0.8	0
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
0.7442	Intermediate Similarity	NPD6902	Approved
0.7326	Intermediate Similarity	NPD6931	Approved
0.7326	Intermediate Similarity	NPD7514	Phase 3
0.7326	Intermediate Similarity	NPD6930	Phase 2
0.7273	Intermediate Similarity	NPD6695	Phase 3
0.7209	Intermediate Similarity	NPD6929	Approved
0.7191	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7332	Phase 2
0.7093	Intermediate Similarity	NPD7145	Approved
0.7024	Intermediate Similarity	NPD6924	Approved
0.7024	Intermediate Similarity	NPD6926	Approved
0.6977	Remote Similarity	NPD5776	Phase 2
0.6977	Remote Similarity	NPD6925	Approved
0.6977	Remote Similarity	NPD6932	Approved
0.6957	Remote Similarity	NPD7750	Discontinued
0.6957	Remote Similarity	NPD7524	Approved
0.6923	Remote Similarity	NPD6893	Approved
0.6923	Remote Similarity	NPD6371	Approved
0.6897	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5362	Discontinued
0.686	Remote Similarity	NPD6933	Approved
0.6824	Remote Similarity	NPD4784	Approved
0.6824	Remote Similarity	NPD4785	Approved
0.6786	Remote Similarity	NPD4243	Approved
0.6742	Remote Similarity	NPD4819	Approved
0.6742	Remote Similarity	NPD4822	Approved
0.6742	Remote Similarity	NPD4820	Approved
0.6742	Remote Similarity	NPD4821	Approved
0.6739	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5785	Approved
0.6705	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5331	Approved
0.6703	Remote Similarity	NPD5332	Approved
0.67	Remote Similarity	NPD7640	Approved
0.67	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD6898	Phase 1
0.6667	Remote Similarity	NPD7143	Approved
0.6632	Remote Similarity	NPD6051	Approved
0.6629	Remote Similarity	NPD6683	Phase 2
0.66	Remote Similarity	NPD7638	Approved
0.6596	Remote Similarity	NPD4251	Approved
0.6596	Remote Similarity	NPD4250	Approved
0.6588	Remote Similarity	NPD7150	Approved
0.6588	Remote Similarity	NPD7151	Approved
0.6588	Remote Similarity	NPD7152	Approved
0.6556	Remote Similarity	NPD7525	Registered
0.6556	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6942	Approved
0.6552	Remote Similarity	NPD7339	Approved
0.6548	Remote Similarity	NPD6923	Approved
0.6548	Remote Similarity	NPD6922	Approved
0.6517	Remote Similarity	NPD4268	Approved
0.6517	Remote Similarity	NPD4271	Approved
0.6495	Remote Similarity	NPD7637	Suspended
0.6489	Remote Similarity	NPD4249	Approved
0.6458	Remote Similarity	NPD1695	Approved
0.6444	Remote Similarity	NPD4195	Approved
0.6413	Remote Similarity	NPD4269	Approved
0.6413	Remote Similarity	NPD4270	Approved
0.6374	Remote Similarity	NPD7509	Discontinued
0.6364	Remote Similarity	NPD5275	Approved
0.6364	Remote Similarity	NPD8264	Approved
0.6364	Remote Similarity	NPD4190	Phase 3
0.6321	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5786	Approved
0.6304	Remote Similarity	NPD5369	Approved
0.6296	Remote Similarity	NPD368	Approved
0.6224	Remote Similarity	NPD7838	Discovery
0.6211	Remote Similarity	NPD5363	Approved
0.6196	Remote Similarity	NPD4252	Approved
0.6196	Remote Similarity	NPD4748	Discontinued
0.6182	Remote Similarity	NPD6053	Discontinued
0.617	Remote Similarity	NPD7154	Phase 3
0.6154	Remote Similarity	NPD5344	Discontinued
0.6136	Remote Similarity	NPD4732	Discontinued
0.6105	Remote Similarity	NPD3666	Approved
0.6105	Remote Similarity	NPD3133	Approved
0.6105	Remote Similarity	NPD4786	Approved
0.6105	Remote Similarity	NPD3665	Phase 1
0.6095	Remote Similarity	NPD7632	Discontinued
0.6071	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6435	Approved
0.6064	Remote Similarity	NPD5209	Approved
0.6064	Remote Similarity	NPD4221	Approved
0.6064	Remote Similarity	NPD4223	Phase 3
0.6061	Remote Similarity	NPD7136	Phase 2
0.6058	Remote Similarity	NPD6648	Approved
0.6053	Remote Similarity	NPD7328	Approved
0.6053	Remote Similarity	NPD7327	Approved
0.6042	Remote Similarity	NPD5329	Approved
0.6034	Remote Similarity	NPD7503	Approved
0.6022	Remote Similarity	NPD5368	Approved
0.6	Remote Similarity	NPD7516	Approved
0.5979	Remote Similarity	NPD5690	Phase 2
0.596	Remote Similarity	NPD4753	Phase 2
0.5949	Remote Similarity	NPD342	Phase 1
0.5948	Remote Similarity	NPD7741	Discontinued
0.5948	Remote Similarity	NPD8294	Approved
0.5948	Remote Similarity	NPD8377	Approved
0.5943	Remote Similarity	NPD5211	Phase 2
0.5941	Remote Similarity	NPD4202	Approved
0.5938	Remote Similarity	NPD4197	Approved
0.5926	Remote Similarity	NPD6640	Phase 3
0.5922	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7645	Phase 2
0.59	Remote Similarity	NPD6698	Approved
0.59	Remote Similarity	NPD46	Approved
0.5897	Remote Similarity	NPD8378	Approved
0.5897	Remote Similarity	NPD8296	Approved
0.5897	Remote Similarity	NPD8335	Approved
0.5897	Remote Similarity	NPD8380	Approved
0.5897	Remote Similarity	NPD8379	Approved
0.5897	Remote Similarity	NPD8033	Approved
0.5895	Remote Similarity	NPD3667	Approved
0.5882	Remote Similarity	NPD5282	Discontinued
0.5865	Remote Similarity	NPD6083	Phase 2
0.5865	Remote Similarity	NPD6084	Phase 2
0.5859	Remote Similarity	NPD4518	Approved
0.5849	Remote Similarity	NPD4159	Approved
0.5842	Remote Similarity	NPD6079	Approved
0.5833	Remote Similarity	NPD4788	Approved
0.5833	Remote Similarity	NPD5141	Approved
0.5826	Remote Similarity	NPD7115	Discovery
0.5825	Remote Similarity	NPD5210	Approved
0.5825	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD4629	Approved
0.5825	Remote Similarity	NPD5695	Phase 3
0.5816	Remote Similarity	NPD6684	Approved
0.5816	Remote Similarity	NPD4688	Approved
0.5816	Remote Similarity	NPD5205	Approved
0.5816	Remote Similarity	NPD5280	Approved
0.5816	Remote Similarity	NPD7334	Approved
0.5816	Remote Similarity	NPD4690	Approved
0.5816	Remote Similarity	NPD4138	Approved
0.5816	Remote Similarity	NPD7146	Approved
0.5816	Remote Similarity	NPD4689	Approved
0.5816	Remote Similarity	NPD4693	Phase 3
0.5816	Remote Similarity	NPD4694	Approved
0.5816	Remote Similarity	NPD5330	Approved
0.5816	Remote Similarity	NPD7521	Approved
0.5816	Remote Similarity	NPD5279	Phase 3
0.5816	Remote Similarity	NPD6409	Approved
0.581	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5328	Approved
0.5784	Remote Similarity	NPD5779	Approved
0.5784	Remote Similarity	NPD5778	Approved
0.5784	Remote Similarity	NPD6399	Phase 3
0.5773	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5286	Approved
0.5755	Remote Similarity	NPD4696	Approved
0.5755	Remote Similarity	NPD5285	Approved
0.5743	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6412	Phase 2
0.5714	Remote Similarity	NPD4755	Approved
0.5702	Remote Similarity	NPD7507	Approved
0.5702	Remote Similarity	NPD4632	Approved
0.5701	Remote Similarity	NPD5223	Approved
0.57	Remote Similarity	NPD6903	Approved
0.57	Remote Similarity	NPD4723	Approved
0.57	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4722	Approved
0.5686	Remote Similarity	NPD5693	Phase 1
0.5686	Remote Similarity	NPD7983	Approved
0.5686	Remote Similarity	NPD5281	Approved
0.5686	Remote Similarity	NPD5284	Approved
0.5679	Remote Similarity	NPD4219	Approved
0.5676	Remote Similarity	NPD6686	Approved
0.5676	Remote Similarity	NPD6881	Approved
0.5676	Remote Similarity	NPD6899	Approved
0.5673	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7604	Phase 2
0.566	Remote Similarity	NPD5696	Approved
0.566	Remote Similarity	NPD4225	Approved
0.5657	Remote Similarity	NPD3618	Phase 1
0.5657	Remote Similarity	NPD6098	Approved
0.5657	Remote Similarity	NPD4519	Discontinued
0.5657	Remote Similarity	NPD4623	Approved
0.5652	Remote Similarity	NPD8039	Approved
0.5648	Remote Similarity	NPD5225	Approved
0.5648	Remote Similarity	NPD5226	Approved
0.5648	Remote Similarity	NPD5224	Approved
0.5648	Remote Similarity	NPD4633	Approved
0.5636	Remote Similarity	NPD6675	Approved
0.5636	Remote Similarity	NPD5739	Approved
0.5636	Remote Similarity	NPD6008	Approved
0.5636	Remote Similarity	NPD7128	Approved
0.5636	Remote Similarity	NPD6402	Approved
0.5631	Remote Similarity	NPD5133	Approved
0.5625	Remote Similarity	NPD4692	Approved
0.5625	Remote Similarity	NPD4139	Approved
0.5612	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD4700	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