NPASS Compound

Structure

NPC45957 OpenBabel07101718292D 23 26 0 0 1 0 0 0 0 0999 V2000 5.6315 2.0013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7883 -1.8703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0885 0.0407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6155 -1.5666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9404 2.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9805 1.8095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6840 0.0161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4760 -0.9620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0242 -1.6179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5755 -0.8327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7581 1.5143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9705 -1.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5756 -0.8177 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8179 0.5161 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6013 0.8842 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0748 -0.1530 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0883 0.0108 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9556 -0.2948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0884 0.0258 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4815 -1.0666 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7557 0.3051 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4815 -2.0666 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 11 2 0 0 0 0 2 12 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 12 18 1 0 0 0 0 13 10 1 1 0 0 0 13 23 1 0 0 0 0 14 7 1 6 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 6 0 0 0 16 17 1 0 0 0 0 16 20 1 6 0 0 0 17 19 1 6 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 1 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	338.712
LogP:	4.618
LogD:	4.197
LogS:	-4.233
# Rotatable Bonds:	2
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.803
Synthetic Accessibility Score:	4.914
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:	-4.72
MDCK Permeability:	1.7681573808658868e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.063
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.422
Plasma Protein Binding (PPB):	91.94219970703125%
Volume Distribution (VD):	1.057
Pgp-substrate:	9.415581703186035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.225
CYP1A2-substrate:	0.583
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.199
CYP2C9-substrate:	0.513
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.842
CYP3A4-inhibitor:	0.569
CYP3A4-substrate:	0.335

ADMET: Excretion

Clearance (CL):	12.268
Half-life (T1/2):	0.554

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.354
Drug-inuced Liver Injury (DILI):	0.323
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.322
Maximum Recommended Daily Dose:	0.267
Skin Sensitization:	0.079
Carcinogencity:	0.34
Eye Corrosion:	0.01
Eye Irritation:	0.014
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC45957

Natural Product ID:	NPC45957
*Common Name:**	Boscarterol H
IUPAC Name:	(2S)-2-[[(1S,1aR,4aR,7S,7aS,7bR)-7-hydroxy-1,7-dimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[e]azulen-1-yl]methyl]-4-methyl-2H-furan-5-one
Synonyms:
Standard InCHIKey:	ZVJZJSRGRVMUND-UUKONUISSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-11-5-6-15-17(16-14(11)7-8-20(16,4)22)19(15,3)10-13-9-12(2)18(21)23-13/h9,13-17,22H,1,5-8,10H2,2-4H3/t13-,14+,15-,16+,17-,19+,20+/m1/s1
SMILES:	C=C1CC[C@@H]2[C@H]([C@@H]3[C@H]1CC[C@]3(C)O)[C@@]2(C)C[C@H]1C=C(C)C(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3087760
PubChem CID:	76309888
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
Others	2

Activity Type	# Activity
Cell Line	2
CELL-LINE	1
NON-MOLECULAR	1
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[506158]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[506158]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	24.3	%	PMID[506158]
NPT21742	CELL-LINE	L02	Homo sapiens	Survival	=	68.0	%	PMID[506158]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[506158]

☑ 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 NPC45957 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	204
0.1-0.2	1446
0.2-0.3	7231
0.3-0.4	16129
0.4-0.5	8201
0.5-0.6	6213
0.6-0.7	2900
0.7-0.8	355
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471657
0.8415	Intermediate Similarity	NPC476317
0.8387	Intermediate Similarity	NPC477949
0.8276	Intermediate Similarity	NPC53011
0.8276	Intermediate Similarity	NPC16887
0.8276	Intermediate Similarity	NPC37005
0.8276	Intermediate Similarity	NPC154893
0.8182	Intermediate Similarity	NPC245434
0.8161	Intermediate Similarity	NPC472473
0.8125	Intermediate Similarity	NPC477950
0.8023	Intermediate Similarity	NPC471656
0.8022	Intermediate Similarity	NPC170775
0.7978	Intermediate Similarity	NPC287015
0.7978	Intermediate Similarity	NPC146850
0.7957	Intermediate Similarity	NPC472954
0.7955	Intermediate Similarity	NPC321385
0.7935	Intermediate Similarity	NPC301969
0.7935	Intermediate Similarity	NPC37607
0.7931	Intermediate Similarity	NPC78677
0.7931	Intermediate Similarity	NPC59994
0.7931	Intermediate Similarity	NPC471661
0.7931	Intermediate Similarity	NPC472471
0.7882	Intermediate Similarity	NPC476439
0.7857	Intermediate Similarity	NPC329852
0.7849	Intermediate Similarity	NPC2882
0.7835	Intermediate Similarity	NPC290802
0.7816	Intermediate Similarity	NPC472470
0.7812	Intermediate Similarity	NPC231751
0.7789	Intermediate Similarity	NPC329435
0.7789	Intermediate Similarity	NPC67584
0.7789	Intermediate Similarity	NPC220221
0.7778	Intermediate Similarity	NPC471795
0.7755	Intermediate Similarity	NPC475099
0.7753	Intermediate Similarity	NPC245665
0.7738	Intermediate Similarity	NPC471659
0.7727	Intermediate Similarity	NPC325031
0.7717	Intermediate Similarity	NPC91248
0.7717	Intermediate Similarity	NPC471956
0.7708	Intermediate Similarity	NPC213078
0.7708	Intermediate Similarity	NPC24956
0.7708	Intermediate Similarity	NPC18019
0.7701	Intermediate Similarity	NPC325869
0.7684	Intermediate Similarity	NPC90453
0.7684	Intermediate Similarity	NPC477131
0.7683	Intermediate Similarity	NPC22301
0.7667	Intermediate Similarity	NPC156485
0.7667	Intermediate Similarity	NPC290052
0.7667	Intermediate Similarity	NPC474693
0.7667	Intermediate Similarity	NPC82297
0.766	Intermediate Similarity	NPC290651
0.7647	Intermediate Similarity	NPC113639
0.7634	Intermediate Similarity	NPC212664
0.7629	Intermediate Similarity	NPC213947
0.7629	Intermediate Similarity	NPC108475
0.7629	Intermediate Similarity	NPC170143
0.7629	Intermediate Similarity	NPC161493
0.7614	Intermediate Similarity	NPC80622
0.7609	Intermediate Similarity	NPC191283
0.7609	Intermediate Similarity	NPC471796
0.7604	Intermediate Similarity	NPC476487
0.7604	Intermediate Similarity	NPC469873
0.7604	Intermediate Similarity	NPC476488
0.7604	Intermediate Similarity	NPC37408
0.7604	Intermediate Similarity	NPC52044
0.76	Intermediate Similarity	NPC297617
0.76	Intermediate Similarity	NPC280566
0.76	Intermediate Similarity	NPC183570
0.7582	Intermediate Similarity	NPC284534
0.7582	Intermediate Similarity	NPC475860
0.7582	Intermediate Similarity	NPC204105
0.7582	Intermediate Similarity	NPC471185
0.7582	Intermediate Similarity	NPC300082
0.7582	Intermediate Similarity	NPC473659
0.7582	Intermediate Similarity	NPC474694
0.7579	Intermediate Similarity	NPC37816
0.7576	Intermediate Similarity	NPC268829
0.7576	Intermediate Similarity	NPC247701
0.7576	Intermediate Similarity	NPC25177
0.7576	Intermediate Similarity	NPC222875
0.7576	Intermediate Similarity	NPC295110
0.7561	Intermediate Similarity	NPC276290
0.7558	Intermediate Similarity	NPC471658
0.7556	Intermediate Similarity	NPC471340
0.7556	Intermediate Similarity	NPC311070
0.7551	Intermediate Similarity	NPC181147
0.7551	Intermediate Similarity	NPC221615
0.7551	Intermediate Similarity	NPC98868
0.7526	Intermediate Similarity	NPC98165
0.7525	Intermediate Similarity	NPC272632
0.75	Intermediate Similarity	NPC55304
0.75	Intermediate Similarity	NPC127019
0.75	Intermediate Similarity	NPC281775
0.75	Intermediate Similarity	NPC262133
0.75	Intermediate Similarity	NPC471660
0.75	Intermediate Similarity	NPC471662
0.75	Intermediate Similarity	NPC137253
0.75	Intermediate Similarity	NPC470013
0.75	Intermediate Similarity	NPC470010
0.75	Intermediate Similarity	NPC198853
0.75	Intermediate Similarity	NPC323008
0.75	Intermediate Similarity	NPC474045
0.75	Intermediate Similarity	NPC472467
0.75	Intermediate Similarity	NPC167219
0.75	Intermediate Similarity	NPC56593
0.75	Intermediate Similarity	NPC67493
0.75	Intermediate Similarity	NPC118405
0.75	Intermediate Similarity	NPC15551
0.75	Intermediate Similarity	NPC201725
0.75	Intermediate Similarity	NPC226226
0.75	Intermediate Similarity	NPC261253
0.7475	Intermediate Similarity	NPC472826
0.7475	Intermediate Similarity	NPC201406
0.7475	Intermediate Similarity	NPC227865
0.7475	Intermediate Similarity	NPC130792
0.7474	Intermediate Similarity	NPC133698
0.7474	Intermediate Similarity	NPC221282
0.7473	Intermediate Similarity	NPC475100
0.7471	Intermediate Similarity	NPC471454
0.7471	Intermediate Similarity	NPC186109
0.747	Intermediate Similarity	NPC265574
0.7449	Intermediate Similarity	NPC202705
0.7447	Intermediate Similarity	NPC232747
0.7444	Intermediate Similarity	NPC474291
0.7439	Intermediate Similarity	NPC472266
0.7429	Intermediate Similarity	NPC71680
0.7426	Intermediate Similarity	NPC180204
0.7426	Intermediate Similarity	NPC160583
0.7426	Intermediate Similarity	NPC196471
0.7426	Intermediate Similarity	NPC472821
0.7426	Intermediate Similarity	NPC10232
0.7426	Intermediate Similarity	NPC112009
0.7426	Intermediate Similarity	NPC187302
0.7426	Intermediate Similarity	NPC97487
0.7426	Intermediate Similarity	NPC189588
0.7423	Intermediate Similarity	NPC213698
0.7423	Intermediate Similarity	NPC293052
0.7419	Intermediate Similarity	NPC201658
0.7419	Intermediate Similarity	NPC312561
0.7416	Intermediate Similarity	NPC276356
0.7404	Intermediate Similarity	NPC47951
0.7404	Intermediate Similarity	NPC477102
0.74	Intermediate Similarity	NPC150923
0.74	Intermediate Similarity	NPC171759
0.7391	Intermediate Similarity	NPC65661
0.7391	Intermediate Similarity	NPC86316
0.7391	Intermediate Similarity	NPC106416
0.7386	Intermediate Similarity	NPC184737
0.7386	Intermediate Similarity	NPC253749
0.7381	Intermediate Similarity	NPC469660
0.7374	Intermediate Similarity	NPC477355
0.7374	Intermediate Similarity	NPC471610
0.7374	Intermediate Similarity	NPC222011
0.7368	Intermediate Similarity	NPC49946
0.7368	Intermediate Similarity	NPC472466
0.7368	Intermediate Similarity	NPC469368
0.7368	Intermediate Similarity	NPC306168
0.7368	Intermediate Similarity	NPC54065
0.7368	Intermediate Similarity	NPC297474
0.7368	Intermediate Similarity	NPC310479
0.7368	Intermediate Similarity	NPC182136
0.7363	Intermediate Similarity	NPC477667
0.7363	Intermediate Similarity	NPC472377
0.7363	Intermediate Similarity	NPC30502
0.7363	Intermediate Similarity	NPC474809
0.7358	Intermediate Similarity	NPC241477
0.7356	Intermediate Similarity	NPC472472
0.7353	Intermediate Similarity	NPC200861
0.7353	Intermediate Similarity	NPC472822
0.7353	Intermediate Similarity	NPC309190
0.7347	Intermediate Similarity	NPC9812
0.734	Intermediate Similarity	NPC79549
0.7333	Intermediate Similarity	NPC477103
0.7333	Intermediate Similarity	NPC257240
0.7326	Intermediate Similarity	NPC474758
0.732	Intermediate Similarity	NPC96541
0.732	Intermediate Similarity	NPC471994
0.732	Intermediate Similarity	NPC120351
0.732	Intermediate Similarity	NPC166143
0.7312	Intermediate Similarity	NPC64153
0.7312	Intermediate Similarity	NPC477668
0.7312	Intermediate Similarity	NPC471219
0.7312	Intermediate Similarity	NPC131813
0.7303	Intermediate Similarity	NPC182550
0.7303	Intermediate Similarity	NPC469690
0.73	Intermediate Similarity	NPC79631
0.73	Intermediate Similarity	NPC476303
0.73	Intermediate Similarity	NPC280963
0.73	Intermediate Similarity	NPC469864
0.73	Intermediate Similarity	NPC469872
0.7292	Intermediate Similarity	NPC74296
0.7292	Intermediate Similarity	NPC472814
0.7292	Intermediate Similarity	NPC171360
0.7292	Intermediate Similarity	NPC29821
0.7292	Intermediate Similarity	NPC293001
0.7292	Intermediate Similarity	NPC35959
0.7292	Intermediate Similarity	NPC63193
0.7292	Intermediate Similarity	NPC177037
0.7292	Intermediate Similarity	NPC110923
0.7292	Intermediate Similarity	NPC133888
0.7292	Intermediate Similarity	NPC472953

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 NPC45957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	2071
0.2-0.3	4262
0.3-0.4	1897
0.4-0.5	397
0.5-0.6	260
0.6-0.7	66
0.7-0.8	6
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
0.7582	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5785	Approved
0.7333	Intermediate Similarity	NPD6371	Approved
0.7263	Intermediate Similarity	NPD1695	Approved
0.7253	Intermediate Similarity	NPD5209	Approved
0.7195	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5362	Discontinued
0.7083	Intermediate Similarity	NPD6051	Approved
0.7071	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7638	Approved
0.6989	Remote Similarity	NPD5332	Approved
0.6989	Remote Similarity	NPD5331	Approved
0.6961	Remote Similarity	NPD7639	Approved
0.6961	Remote Similarity	NPD7640	Approved
0.6957	Remote Similarity	NPD4790	Discontinued
0.69	Remote Similarity	NPD5695	Phase 3
0.6848	Remote Similarity	NPD4821	Approved
0.6848	Remote Similarity	NPD4820	Approved
0.6848	Remote Similarity	NPD4822	Approved
0.6848	Remote Similarity	NPD4819	Approved
0.6848	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5363	Approved
0.6813	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6903	Approved
0.6771	Remote Similarity	NPD7146	Approved
0.6771	Remote Similarity	NPD7334	Approved
0.6771	Remote Similarity	NPD5330	Approved
0.6771	Remote Similarity	NPD7521	Approved
0.6771	Remote Similarity	NPD6409	Approved
0.6771	Remote Similarity	NPD6684	Approved
0.6768	Remote Similarity	NPD5693	Phase 1
0.6765	Remote Similarity	NPD6084	Phase 2
0.6765	Remote Similarity	NPD6083	Phase 2
0.6739	Remote Similarity	NPD4195	Approved
0.6733	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6053	Discontinued
0.6699	Remote Similarity	NPD4225	Approved
0.6699	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6634	Remote Similarity	NPD6001	Approved
0.6633	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4268	Approved
0.663	Remote Similarity	NPD4271	Approved
0.6598	Remote Similarity	NPD4249	Approved
0.6596	Remote Similarity	NPD5369	Approved
0.6579	Remote Similarity	NPD7328	Approved
0.6579	Remote Similarity	NPD7327	Approved
0.6574	Remote Similarity	NPD5697	Approved
0.6562	Remote Similarity	NPD3666	Approved
0.6562	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3665	Phase 1
0.6562	Remote Similarity	NPD3133	Approved
0.6531	Remote Similarity	NPD4250	Approved
0.6531	Remote Similarity	NPD4251	Approved
0.6526	Remote Similarity	NPD6435	Approved
0.6526	Remote Similarity	NPD4270	Approved
0.6526	Remote Similarity	NPD4269	Approved
0.6526	Remote Similarity	NPD4221	Approved
0.6526	Remote Similarity	NPD4223	Phase 3
0.6522	Remote Similarity	NPD7516	Approved
0.6514	Remote Similarity	NPD7320	Approved
0.6514	Remote Similarity	NPD6881	Approved
0.6514	Remote Similarity	NPD6899	Approved
0.6514	Remote Similarity	NPD6011	Approved
0.65	Remote Similarity	NPD5207	Approved
0.6491	Remote Similarity	NPD7115	Discovery
0.6481	Remote Similarity	NPD6402	Approved
0.6481	Remote Similarity	NPD5739	Approved
0.6481	Remote Similarity	NPD7128	Approved
0.6481	Remote Similarity	NPD6675	Approved
0.6466	Remote Similarity	NPD8377	Approved
0.6466	Remote Similarity	NPD8294	Approved
0.6465	Remote Similarity	NPD5208	Approved
0.6458	Remote Similarity	NPD7154	Phase 3
0.6455	Remote Similarity	NPD6013	Approved
0.6455	Remote Similarity	NPD6014	Approved
0.6455	Remote Similarity	NPD6012	Approved
0.6436	Remote Similarity	NPD5284	Approved
0.6436	Remote Similarity	NPD7637	Suspended
0.6436	Remote Similarity	NPD5281	Approved
0.6429	Remote Similarity	NPD5690	Phase 2
0.6429	Remote Similarity	NPD5786	Approved
0.6422	Remote Similarity	NPD5701	Approved
0.641	Remote Similarity	NPD8296	Approved
0.641	Remote Similarity	NPD8380	Approved
0.641	Remote Similarity	NPD8033	Approved
0.641	Remote Similarity	NPD8378	Approved
0.641	Remote Similarity	NPD8379	Approved
0.641	Remote Similarity	NPD8335	Approved
0.64	Remote Similarity	NPD6080	Approved
0.64	Remote Similarity	NPD4753	Phase 2
0.64	Remote Similarity	NPD6673	Approved
0.64	Remote Similarity	NPD6904	Approved
0.6396	Remote Similarity	NPD7102	Approved
0.6396	Remote Similarity	NPD7290	Approved
0.6396	Remote Similarity	NPD6883	Approved
0.6392	Remote Similarity	NPD4197	Approved
0.6374	Remote Similarity	NPD6926	Approved
0.6374	Remote Similarity	NPD6924	Approved
0.6373	Remote Similarity	NPD6399	Phase 3
0.6373	Remote Similarity	NPD4202	Approved
0.6364	Remote Similarity	NPD6686	Approved
0.6355	Remote Similarity	NPD7632	Discontinued
0.6339	Remote Similarity	NPD6617	Approved
0.6339	Remote Similarity	NPD8130	Phase 1
0.6339	Remote Similarity	NPD6650	Approved
0.6339	Remote Similarity	NPD6847	Approved
0.6339	Remote Similarity	NPD6649	Approved
0.6339	Remote Similarity	NPD6869	Approved
0.6337	Remote Similarity	NPD46	Approved
0.6337	Remote Similarity	NPD6698	Approved
0.6337	Remote Similarity	NPD5692	Phase 3
0.6333	Remote Similarity	NPD7507	Approved
0.633	Remote Similarity	NPD6008	Approved
0.6327	Remote Similarity	NPD5329	Approved
0.6316	Remote Similarity	NPD5368	Approved
0.6316	Remote Similarity	NPD4252	Approved
0.6306	Remote Similarity	NPD6373	Approved
0.6306	Remote Similarity	NPD6372	Approved
0.63	Remote Similarity	NPD5737	Approved
0.63	Remote Similarity	NPD6672	Approved
0.6289	Remote Similarity	NPD6695	Phase 3
0.6283	Remote Similarity	NPD8297	Approved
0.6283	Remote Similarity	NPD6882	Approved
0.6275	Remote Similarity	NPD6050	Approved
0.6275	Remote Similarity	NPD5694	Approved
0.6271	Remote Similarity	NPD7503	Approved
0.6263	Remote Similarity	NPD4138	Approved
0.6263	Remote Similarity	NPD5205	Approved
0.6263	Remote Similarity	NPD4690	Approved
0.6263	Remote Similarity	NPD5279	Phase 3
0.6263	Remote Similarity	NPD6098	Approved
0.6263	Remote Similarity	NPD4694	Approved
0.6263	Remote Similarity	NPD4693	Phase 3
0.6263	Remote Similarity	NPD5280	Approved
0.6263	Remote Similarity	NPD4689	Approved
0.6263	Remote Similarity	NPD4688	Approved
0.6262	Remote Similarity	NPD5344	Discontinued
0.625	Remote Similarity	NPD4629	Approved
0.625	Remote Similarity	NPD5210	Approved
0.6237	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6933	Approved
0.6224	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5211	Phase 2
0.62	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD7319	Approved
0.6168	Remote Similarity	NPD5285	Approved
0.6168	Remote Similarity	NPD5286	Approved
0.6168	Remote Similarity	NPD6648	Approved
0.6168	Remote Similarity	NPD4696	Approved
0.6162	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4243	Approved
0.6146	Remote Similarity	NPD6930	Phase 2
0.6146	Remote Similarity	NPD6931	Approved
0.6139	Remote Similarity	NPD4518	Approved
0.6132	Remote Similarity	NPD4755	Approved
0.6132	Remote Similarity	NPD5959	Approved
0.6129	Remote Similarity	NPD8039	Approved
0.6122	Remote Similarity	NPD4788	Approved
0.6121	Remote Similarity	NPD6274	Approved
0.6117	Remote Similarity	NPD6079	Approved
0.6111	Remote Similarity	NPD5223	Approved
0.61	Remote Similarity	NPD3618	Phase 1
0.6091	Remote Similarity	NPD5141	Approved
0.6087	Remote Similarity	NPD4632	Approved
0.6082	Remote Similarity	NPD6902	Approved
0.6078	Remote Similarity	NPD5328	Approved
0.6075	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6317	Approved
0.6061	Remote Similarity	NPD4786	Approved
0.6058	Remote Similarity	NPD5133	Approved
0.6055	Remote Similarity	NPD4633	Approved
0.6055	Remote Similarity	NPD5224	Approved
0.6055	Remote Similarity	NPD5225	Approved
0.6055	Remote Similarity	NPD5226	Approved
0.6042	Remote Similarity	NPD6929	Approved
0.604	Remote Similarity	NPD7524	Approved
0.604	Remote Similarity	NPD7750	Discontinued
0.6038	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD7604	Phase 2
0.6022	Remote Similarity	NPD4784	Approved
0.6022	Remote Similarity	NPD4785	Approved
0.602	Remote Similarity	NPD3667	Approved
0.6019	Remote Similarity	NPD4700	Approved
0.6019	Remote Similarity	NPD4096	Approved
0.6018	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6335	Approved
0.6017	Remote Similarity	NPD6313	Approved
0.6017	Remote Similarity	NPD6314	Approved
0.6	Remote Similarity	NPD5282	Discontinued
0.6	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD5174	Approved
0.6	Remote Similarity	NPD1696	Phase 3
0.6	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7748	Approved
0.5979	Remote Similarity	NPD7514	Phase 3

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