NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	263.658
LogP:	1.009
LogD:	0.914
LogS:	-4.0
# Rotatable Bonds:	1
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.781
Synthetic Accessibility Score:	6.34
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.098
MDCK Permeability:	3.736298458534293e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.055
30% Bioavailability (F30%):	0.093

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.936
Plasma Protein Binding (PPB):	58.43421173095703%
Volume Distribution (VD):	1.323
Pgp-substrate:	57.57783508300781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.106
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.07
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.316
CYP3A4-inhibitor:	0.133
CYP3A4-substrate:	0.828

ADMET: Excretion

Clearance (CL):	8.298
Half-life (T1/2):	0.861

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.777
Drug-inuced Liver Injury (DILI):	0.076
AMES Toxicity:	0.639
Rat Oral Acute Toxicity:	0.183
Maximum Recommended Daily Dose:	0.764
Skin Sensitization:	0.817
Carcinogencity:	0.911
Eye Corrosion:	0.014
Eye Irritation:	0.79
Respiratory Toxicity:	0.778

Download Data

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

Natural Product: NPC10150

Natural Product ID:	NPC10150
*Common Name:**	Loukacinol B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KTGHJWMKLMSJIQ-KJWHEZOQSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-9-6-15-13(3,7-10(9)17)12(2)5-4-11(18-15)14(12,8-16)19-15/h6,11,16H,4-5,7-8H2,1-3H3/t11-,12-,13-,14-,15-/m1/s1
SMILES:	OC[C@@]12O[C@@]34O[C@@H]1CC[C@]2(C)[C@@]3(C)CC(=O)C(=C4)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520763
PubChem CID:	10825510
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650079]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441070]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	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
EC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	11.8	ug.mL-1	PMID[521283]
NPT2359	Cell Line	SK-MEL-30	Homo sapiens	EC50	=	13.6	ug.mL-1	PMID[521283]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	15.2	ug.mL-1	PMID[521283]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	13.3	ug.mL-1	PMID[521283]

☑ 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 NPC10150 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	247
0.1-0.2	1431
0.2-0.3	5534
0.3-0.4	10140
0.4-0.5	13545
0.5-0.6	7408
0.6-0.7	3887
0.7-0.8	496
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.99	High Similarity	NPC187876
0.9515	High Similarity	NPC474750
0.8654	High Similarity	NPC123505
0.8519	High Similarity	NPC41551
0.8519	High Similarity	NPC50223
0.8426	Intermediate Similarity	NPC77089
0.8142	Intermediate Similarity	NPC277583
0.8056	Intermediate Similarity	NPC169843
0.8036	Intermediate Similarity	NPC471570
0.8	Intermediate Similarity	NPC475960
0.8	Intermediate Similarity	NPC473888
0.7982	Intermediate Similarity	NPC138372
0.7982	Intermediate Similarity	NPC106228
0.7963	Intermediate Similarity	NPC474775
0.7944	Intermediate Similarity	NPC150923
0.7899	Intermediate Similarity	NPC144625
0.7895	Intermediate Similarity	NPC471398
0.7886	Intermediate Similarity	NPC224623
0.785	Intermediate Similarity	NPC70865
0.7818	Intermediate Similarity	NPC54737
0.7807	Intermediate Similarity	NPC178981
0.7798	Intermediate Similarity	NPC110989
0.7788	Intermediate Similarity	NPC81419
0.7788	Intermediate Similarity	NPC179746
0.7787	Intermediate Similarity	NPC13071
0.7778	Intermediate Similarity	NPC9674
0.7778	Intermediate Similarity	NPC171759
0.7778	Intermediate Similarity	NPC19028
0.7757	Intermediate Similarity	NPC177232
0.7757	Intermediate Similarity	NPC187268
0.7757	Intermediate Similarity	NPC212465
0.7739	Intermediate Similarity	NPC326542
0.7727	Intermediate Similarity	NPC100487
0.7727	Intermediate Similarity	NPC474917
0.7727	Intermediate Similarity	NPC203659
0.7724	Intermediate Similarity	NPC469351
0.7719	Intermediate Similarity	NPC207251
0.7719	Intermediate Similarity	NPC126691
0.7712	Intermediate Similarity	NPC474585
0.7712	Intermediate Similarity	NPC79579
0.7706	Intermediate Similarity	NPC225353
0.7706	Intermediate Similarity	NPC86077
0.7706	Intermediate Similarity	NPC70369
0.7699	Intermediate Similarity	NPC5103
0.7692	Intermediate Similarity	NPC12172
0.7692	Intermediate Similarity	NPC208886
0.7685	Intermediate Similarity	NPC79631
0.7667	Intermediate Similarity	NPC471392
0.7664	Intermediate Similarity	NPC266842
0.7664	Intermediate Similarity	NPC471150
0.7664	Intermediate Similarity	NPC311904
0.7658	Intermediate Similarity	NPC243998
0.7652	Intermediate Similarity	NPC287075
0.7642	Intermediate Similarity	NPC52044
0.7636	Intermediate Similarity	NPC124881
0.7636	Intermediate Similarity	NPC260809
0.7636	Intermediate Similarity	NPC472747
0.7636	Intermediate Similarity	NPC472750
0.7636	Intermediate Similarity	NPC474783
0.7627	Intermediate Similarity	NPC475834
0.7627	Intermediate Similarity	NPC474179
0.7619	Intermediate Similarity	NPC475912
0.7615	Intermediate Similarity	NPC471401
0.7611	Intermediate Similarity	NPC59489
0.7611	Intermediate Similarity	NPC139838
0.7593	Intermediate Similarity	NPC473326
0.7586	Intermediate Similarity	NPC305044
0.7586	Intermediate Similarity	NPC265290
0.7586	Intermediate Similarity	NPC474181
0.7583	Intermediate Similarity	NPC28532
0.7583	Intermediate Similarity	NPC313528
0.7581	Intermediate Similarity	NPC213634
0.757	Intermediate Similarity	NPC126156
0.757	Intermediate Similarity	NPC18019
0.757	Intermediate Similarity	NPC24956
0.7568	Intermediate Similarity	NPC296950
0.7568	Intermediate Similarity	NPC472748
0.7568	Intermediate Similarity	NPC100955
0.7568	Intermediate Similarity	NPC121566
0.7568	Intermediate Similarity	NPC258532
0.7565	Intermediate Similarity	NPC313921
0.7565	Intermediate Similarity	NPC98038
0.7561	Intermediate Similarity	NPC311534
0.7561	Intermediate Similarity	NPC172823
0.7545	Intermediate Similarity	NPC223834
0.7545	Intermediate Similarity	NPC252242
0.7545	Intermediate Similarity	NPC475956
0.7544	Intermediate Similarity	NPC235014
0.7542	Intermediate Similarity	NPC153440
0.7542	Intermediate Similarity	NPC475372
0.7542	Intermediate Similarity	NPC13710
0.7542	Intermediate Similarity	NPC475913
0.7542	Intermediate Similarity	NPC475401
0.754	Intermediate Similarity	NPC471234
0.7524	Intermediate Similarity	NPC30515
0.7524	Intermediate Similarity	NPC184463
0.7523	Intermediate Similarity	NPC471381
0.7522	Intermediate Similarity	NPC473288
0.7522	Intermediate Similarity	NPC472825
0.7521	Intermediate Similarity	NPC266728
0.7521	Intermediate Similarity	NPC49492
0.7521	Intermediate Similarity	NPC129992
0.7521	Intermediate Similarity	NPC190286
0.7521	Intermediate Similarity	NPC1538
0.7521	Intermediate Similarity	NPC27363
0.752	Intermediate Similarity	NPC471855
0.75	Intermediate Similarity	NPC469401
0.75	Intermediate Similarity	NPC477944
0.75	Intermediate Similarity	NPC473228
0.75	Intermediate Similarity	NPC469463
0.75	Intermediate Similarity	NPC223450
0.75	Intermediate Similarity	NPC91695
0.75	Intermediate Similarity	NPC95243
0.75	Intermediate Similarity	NPC96377
0.75	Intermediate Similarity	NPC70145
0.75	Intermediate Similarity	NPC108475
0.75	Intermediate Similarity	NPC470829
0.75	Intermediate Similarity	NPC472749
0.75	Intermediate Similarity	NPC213947
0.75	Intermediate Similarity	NPC473564
0.75	Intermediate Similarity	NPC469454
0.75	Intermediate Similarity	NPC42675
0.75	Intermediate Similarity	NPC101965
0.75	Intermediate Similarity	NPC472001
0.75	Intermediate Similarity	NPC170143
0.75	Intermediate Similarity	NPC472290
0.75	Intermediate Similarity	NPC472000
0.75	Intermediate Similarity	NPC317210
0.75	Intermediate Similarity	NPC312017
0.75	Intermediate Similarity	NPC471999
0.75	Intermediate Similarity	NPC469496
0.75	Intermediate Similarity	NPC472751
0.75	Intermediate Similarity	NPC46570
0.75	Intermediate Similarity	NPC63023
0.75	Intermediate Similarity	NPC161493
0.75	Intermediate Similarity	NPC9848
0.75	Intermediate Similarity	NPC101400
0.748	Intermediate Similarity	NPC42399
0.748	Intermediate Similarity	NPC11732
0.748	Intermediate Similarity	NPC287423
0.748	Intermediate Similarity	NPC152091
0.7479	Intermediate Similarity	NPC477092
0.7479	Intermediate Similarity	NPC5292
0.7479	Intermediate Similarity	NPC475041
0.7479	Intermediate Similarity	NPC312536
0.7478	Intermediate Similarity	NPC179798
0.7478	Intermediate Similarity	NPC304180
0.7477	Intermediate Similarity	NPC475321
0.7477	Intermediate Similarity	NPC36954
0.7477	Intermediate Similarity	NPC270013
0.7477	Intermediate Similarity	NPC14961
0.7477	Intermediate Similarity	NPC170120
0.7477	Intermediate Similarity	NPC475945
0.7477	Intermediate Similarity	NPC151516
0.7477	Intermediate Similarity	NPC213698
0.7477	Intermediate Similarity	NPC475871
0.7477	Intermediate Similarity	NPC240838
0.7477	Intermediate Similarity	NPC37408
0.7477	Intermediate Similarity	NPC67584
0.746	Intermediate Similarity	NPC88668
0.7459	Intermediate Similarity	NPC190846
0.7459	Intermediate Similarity	NPC277191
0.7458	Intermediate Similarity	NPC475305
0.7458	Intermediate Similarity	NPC475323
0.7458	Intermediate Similarity	NPC23046
0.7458	Intermediate Similarity	NPC473656
0.7458	Intermediate Similarity	NPC218970
0.7455	Intermediate Similarity	NPC475099
0.7455	Intermediate Similarity	NPC477950
0.7455	Intermediate Similarity	NPC26557
0.7453	Intermediate Similarity	NPC476300
0.7453	Intermediate Similarity	NPC135776
0.7453	Intermediate Similarity	NPC212486
0.7438	Intermediate Similarity	NPC107493
0.7438	Intermediate Similarity	NPC192309
0.7436	Intermediate Similarity	NPC123117
0.7436	Intermediate Similarity	NPC471380
0.7436	Intermediate Similarity	NPC178289
0.7431	Intermediate Similarity	NPC474957
0.7431	Intermediate Similarity	NPC222303
0.7431	Intermediate Similarity	NPC470541
0.7431	Intermediate Similarity	NPC23364
0.7431	Intermediate Similarity	NPC79449
0.7429	Intermediate Similarity	NPC51004
0.7417	Intermediate Similarity	NPC143755
0.7414	Intermediate Similarity	NPC236217
0.7411	Intermediate Similarity	NPC228669
0.7411	Intermediate Similarity	NPC146731
0.7411	Intermediate Similarity	NPC307846
0.7411	Intermediate Similarity	NPC164835
0.7411	Intermediate Similarity	NPC305157
0.7411	Intermediate Similarity	NPC255309
0.7407	Intermediate Similarity	NPC8803
0.7407	Intermediate Similarity	NPC213078
0.7407	Intermediate Similarity	NPC142529
0.7407	Intermediate Similarity	NPC91771
0.7404	Intermediate Similarity	NPC202672
0.7398	Intermediate Similarity	NPC93368
0.7398	Intermediate Similarity	NPC469750
0.7398	Intermediate Similarity	NPC250556

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 NPC10150 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	2114
0.2-0.3	3980
0.3-0.4	1954
0.4-0.5	528
0.5-0.6	232
0.6-0.7	104
0.7-0.8	10
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
0.7712	Intermediate Similarity	NPD6054	Approved
0.7647	Intermediate Similarity	NPD6015	Approved
0.7647	Intermediate Similarity	NPD6016	Approved
0.7589	Intermediate Similarity	NPD6412	Phase 2
0.7583	Intermediate Similarity	NPD6370	Approved
0.7583	Intermediate Similarity	NPD5988	Approved
0.7563	Intermediate Similarity	NPD6059	Approved
0.748	Intermediate Similarity	NPD7078	Approved
0.7459	Intermediate Similarity	NPD7492	Approved
0.7398	Intermediate Similarity	NPD6616	Approved
0.7398	Intermediate Similarity	NPD7507	Approved
0.7281	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD7736	Approved
0.7241	Intermediate Similarity	NPD6371	Approved
0.7222	Intermediate Similarity	NPD7319	Approved
0.7217	Intermediate Similarity	NPD6686	Approved
0.72	Intermediate Similarity	NPD8293	Discontinued
0.7167	Intermediate Similarity	NPD6009	Approved
0.7156	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6319	Approved
0.7119	Intermediate Similarity	NPD6053	Discontinued
0.7059	Intermediate Similarity	NPD4632	Approved
0.7008	Intermediate Similarity	NPD6033	Approved
0.6975	Remote Similarity	NPD6882	Approved
0.6949	Remote Similarity	NPD4634	Approved
0.6899	Remote Similarity	NPD5956	Approved
0.6897	Remote Similarity	NPD6008	Approved
0.6838	Remote Similarity	NPD5697	Approved
0.6833	Remote Similarity	NPD8297	Approved
0.6829	Remote Similarity	NPD7327	Approved
0.6829	Remote Similarity	NPD7328	Approved
0.6825	Remote Similarity	NPD6067	Discontinued
0.68	Remote Similarity	NPD7503	Approved
0.6789	Remote Similarity	NPD6698	Approved
0.6789	Remote Similarity	NPD5785	Approved
0.6789	Remote Similarity	NPD46	Approved
0.6783	Remote Similarity	NPD5211	Phase 2
0.678	Remote Similarity	NPD6899	Approved
0.678	Remote Similarity	NPD6881	Approved
0.678	Remote Similarity	NPD7320	Approved
0.6774	Remote Similarity	NPD7516	Approved
0.6757	Remote Similarity	NPD5282	Discontinued
0.6754	Remote Similarity	NPD5286	Approved
0.6754	Remote Similarity	NPD5285	Approved
0.6754	Remote Similarity	NPD4696	Approved
0.6752	Remote Similarity	NPD6675	Approved
0.6752	Remote Similarity	NPD7128	Approved
0.6752	Remote Similarity	NPD6402	Approved
0.6752	Remote Similarity	NPD5739	Approved
0.675	Remote Similarity	NPD6650	Approved
0.675	Remote Similarity	NPD6649	Approved
0.6748	Remote Similarity	NPD7115	Discovery
0.6726	Remote Similarity	NPD4755	Approved
0.6723	Remote Similarity	NPD6373	Approved
0.6723	Remote Similarity	NPD6014	Approved
0.6723	Remote Similarity	NPD6012	Approved
0.6723	Remote Similarity	NPD6013	Approved
0.6723	Remote Similarity	NPD6372	Approved
0.672	Remote Similarity	NPD8377	Approved
0.672	Remote Similarity	NPD8294	Approved
0.6697	Remote Similarity	NPD1695	Approved
0.6695	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6639	Remote Similarity	NPD6011	Approved
0.6638	Remote Similarity	NPD5226	Approved
0.6638	Remote Similarity	NPD5224	Approved
0.6638	Remote Similarity	NPD5225	Approved
0.6638	Remote Similarity	NPD4633	Approved
0.6636	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1694	Approved
0.6612	Remote Similarity	NPD6847	Approved
0.6612	Remote Similarity	NPD6617	Approved
0.6612	Remote Similarity	NPD8130	Phase 1
0.6612	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6869	Approved
0.6609	Remote Similarity	NPD7640	Approved
0.6609	Remote Similarity	NPD4700	Approved
0.6609	Remote Similarity	NPD7639	Approved
0.6583	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5174	Approved
0.6581	Remote Similarity	NPD5175	Approved
0.6579	Remote Similarity	NPD6083	Phase 2
0.6579	Remote Similarity	NPD6084	Phase 2
0.6562	Remote Similarity	NPD7604	Phase 2
0.6552	Remote Similarity	NPD5223	Approved
0.6549	Remote Similarity	NPD5695	Phase 3
0.6549	Remote Similarity	NPD4629	Approved
0.6549	Remote Similarity	NPD5210	Approved
0.6545	Remote Similarity	NPD4753	Phase 2
0.6542	Remote Similarity	NPD3666	Approved
0.6542	Remote Similarity	NPD3133	Approved
0.6542	Remote Similarity	NPD3665	Phase 1
0.6522	Remote Similarity	NPD4225	Approved
0.6522	Remote Similarity	NPD5696	Approved
0.6522	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6435	Approved
0.6462	Remote Similarity	NPD6336	Discontinued
0.6434	Remote Similarity	NPD8328	Phase 3
0.6422	Remote Similarity	NPD4249	Approved
0.6412	Remote Similarity	NPD8074	Phase 3
0.6406	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6274	Approved
0.6393	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4202	Approved
0.6371	Remote Similarity	NPD8133	Approved
0.6364	Remote Similarity	NPD4250	Approved
0.6364	Remote Similarity	NPD5128	Approved
0.6364	Remote Similarity	NPD4251	Approved
0.6364	Remote Similarity	NPD4729	Approved
0.6364	Remote Similarity	NPD4730	Approved
0.6343	Remote Similarity	NPD7260	Phase 2
0.6341	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7838	Discovery
0.6333	Remote Similarity	NPD4768	Approved
0.6333	Remote Similarity	NPD4767	Approved
0.633	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5363	Approved
0.6321	Remote Similarity	NPD5368	Approved
0.6306	Remote Similarity	NPD6903	Approved
0.6303	Remote Similarity	NPD4754	Approved
0.6296	Remote Similarity	NPD6845	Suspended
0.6283	Remote Similarity	NPD6079	Approved
0.6283	Remote Similarity	NPD5693	Phase 1
0.6283	Remote Similarity	NPD5281	Approved
0.6283	Remote Similarity	NPD5284	Approved
0.6283	Remote Similarity	NPD7983	Approved
0.6273	Remote Similarity	NPD7146	Approved
0.6273	Remote Similarity	NPD7521	Approved
0.6273	Remote Similarity	NPD5330	Approved
0.6273	Remote Similarity	NPD5786	Approved
0.6273	Remote Similarity	NPD6684	Approved
0.6273	Remote Similarity	NPD6409	Approved
0.6273	Remote Similarity	NPD7334	Approved
0.6273	Remote Similarity	NPD3618	Phase 1
0.6261	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5250	Approved
0.626	Remote Similarity	NPD5247	Approved
0.626	Remote Similarity	NPD5248	Approved
0.626	Remote Similarity	NPD5249	Phase 3
0.626	Remote Similarity	NPD5251	Approved
0.625	Remote Similarity	NPD7100	Approved
0.625	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD7101	Approved
0.625	Remote Similarity	NPD4522	Approved
0.6232	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6399	Phase 3
0.622	Remote Similarity	NPD6317	Approved
0.621	Remote Similarity	NPD5217	Approved
0.621	Remote Similarity	NPD5215	Approved
0.621	Remote Similarity	NPD5216	Approved
0.6207	Remote Similarity	NPD4697	Phase 3
0.6207	Remote Similarity	NPD5221	Approved
0.6207	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5222	Approved
0.6204	Remote Similarity	NPD4223	Phase 3
0.6204	Remote Similarity	NPD4221	Approved
0.6195	Remote Similarity	NPD5207	Approved
0.6183	Remote Similarity	NPD7642	Approved
0.6179	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6335	Approved
0.6172	Remote Similarity	NPD6313	Approved
0.6172	Remote Similarity	NPD6314	Approved
0.6161	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5173	Approved
0.6148	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6110	Phase 1
0.6147	Remote Similarity	NPD5362	Discontinued
0.6134	Remote Similarity	NPD5344	Discontinued
0.6129	Remote Similarity	NPD5135	Approved
0.6129	Remote Similarity	NPD5169	Approved
0.6129	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5690	Phase 2
0.6116	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5369	Approved
0.6091	Remote Similarity	NPD4197	Approved
0.6087	Remote Similarity	NPD5778	Approved
0.6087	Remote Similarity	NPD5779	Approved
0.6083	Remote Similarity	NPD7632	Discontinued
0.608	Remote Similarity	NPD5127	Approved
0.6055	Remote Similarity	NPD3667	Approved
0.6055	Remote Similarity	NPD4269	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