NPASS Compound

Structure

NPC469688 OpenBabel07101719512D 23 24 0 0 1 0 0 0 0 0999 V2000 0.5195 1.6523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1712 1.2761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4725 -3.6797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9523 1.3454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7898 -1.1405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9600 -2.1547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4805 0.7151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5355 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3317 -1.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1466 -2.7823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2805 -2.2823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1538 -1.6107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 0.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1454 -2.7347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4523 0.4793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9174 -0.3980 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6620 -0.7495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1424 -0.2444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8223 -1.3935 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6575 -0.6544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8725 -0.3268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0313 0.2138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 20 1 0 0 0 0 13 19 2 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 1 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 23 1 6 0 0 0 20 5 1 1 0 0 0 22 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	3.679
LogD:	3.757
LogS:	-4.685
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	4.968
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.658
MDCK Permeability:	2.2262636775849387e-05
Pgp-inhibitor:	0.967
Pgp-substrate:	0.768
Human Intestinal Absorption (HIA):	0.74
20% Bioavailability (F20%):	0.825
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.38
Plasma Protein Binding (PPB):	96.7374496459961%
Volume Distribution (VD):	1.003
Pgp-substrate:	2.151012897491455%

ADMET: Metabolism

CYP1A2-inhibitor:	0.086
CYP1A2-substrate:	0.355
CYP2C19-inhibitor:	0.25
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.181
CYP2C9-substrate:	0.626
CYP2D6-inhibitor:	0.246
CYP2D6-substrate:	0.633
CYP3A4-inhibitor:	0.237
CYP3A4-substrate:	0.298

ADMET: Excretion

Clearance (CL):	4.778
Half-life (T1/2):	0.248

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.785
Drug-inuced Liver Injury (DILI):	0.212
AMES Toxicity:	0.461
Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.951
Carcinogencity:	0.362
Eye Corrosion:	0.803
Eye Irritation:	0.642
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC469688

Natural Product ID:	NPC469688
*Common Name:**	7R-Hydroperoxy-13-Keto-1R,11S*-Dolabell-3E,8E,12(18)-Triene
IUPAC Name:	(3aR,5E,9R,10E,12aS)-9-hydroperoxy-3a,6,10-trimethyl-1-propan-2-ylidene-4,7,8,9,12,12a-hexahydro-3H-cyclopenta[11]annulen-2-one
Synonyms:
Standard InCHIKey:	XIWBBVNJGMKOMD-CBDHSLHVSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-13(2)19-16-8-7-15(4)18(23-22)9-6-14(3)10-11-20(16,5)12-17(19)21/h7,10,16,18,22H,6,8-9,11-12H2,1-5H3/b14-10+,15-7+/t16-,18-,20-/m1/s1
SMILES:	OO[C@@H]1CC/C(=C/C[C@]2([C@H](C/C=C/1C)C(=C(C)C)C(=O)C2)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098810
PubChem CID:	46833128
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane 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
NPO32701	Eunicea	Genus	Plexauridae	Eukaryota	n.a.	southwestern Caribbean	n.a.	PMID[20384296]

☑ 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	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	36400.0	nM	PMID[450843]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	<=	50.0	%	PMID[450843]

☑ 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 NPC469688 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	157
0.1-0.2	1363
0.2-0.3	9825
0.3-0.4	15158
0.4-0.5	7645
0.5-0.6	6048
0.6-0.7	2270
0.7-0.8	222
0.8-0.85	6
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9385	High Similarity	NPC469679
0.9242	High Similarity	NPC469677
0.8472	Intermediate Similarity	NPC469646
0.8438	Intermediate Similarity	NPC259261
0.8281	Intermediate Similarity	NPC266295
0.8281	Intermediate Similarity	NPC94991
0.8194	Intermediate Similarity	NPC167049
0.8194	Intermediate Similarity	NPC469691
0.8082	Intermediate Similarity	NPC216791
0.8082	Intermediate Similarity	NPC474011
0.803	Intermediate Similarity	NPC25853
0.7941	Intermediate Similarity	NPC473902
0.7895	Intermediate Similarity	NPC469690
0.7846	Intermediate Similarity	NPC49575
0.7846	Intermediate Similarity	NPC267626
0.7846	Intermediate Similarity	NPC55004
0.7846	Intermediate Similarity	NPC230823
0.7838	Intermediate Similarity	NPC469678
0.7838	Intermediate Similarity	NPC475771
0.7838	Intermediate Similarity	NPC469669
0.7808	Intermediate Similarity	NPC107783
0.7808	Intermediate Similarity	NPC92909
0.7763	Intermediate Similarity	NPC475994
0.7727	Intermediate Similarity	NPC30215
0.7692	Intermediate Similarity	NPC136150
0.7681	Intermediate Similarity	NPC212210
0.7671	Intermediate Similarity	NPC474884
0.7662	Intermediate Similarity	NPC469620
0.7662	Intermediate Similarity	NPC229204
0.7647	Intermediate Similarity	NPC260573
0.7647	Intermediate Similarity	NPC97322
0.7647	Intermediate Similarity	NPC475795
0.7639	Intermediate Similarity	NPC61702
0.7639	Intermediate Similarity	NPC162867
0.7632	Intermediate Similarity	NPC86917
0.7632	Intermediate Similarity	NPC276769
0.7625	Intermediate Similarity	NPC230527
0.7625	Intermediate Similarity	NPC7927
0.76	Intermediate Similarity	NPC251435
0.7571	Intermediate Similarity	NPC474329
0.7571	Intermediate Similarity	NPC474304
0.7568	Intermediate Similarity	NPC186042
0.7564	Intermediate Similarity	NPC45495
0.7561	Intermediate Similarity	NPC287079
0.7536	Intermediate Similarity	NPC32285
0.7536	Intermediate Similarity	NPC165695
0.7534	Intermediate Similarity	NPC286154
0.75	Intermediate Similarity	NPC226242
0.75	Intermediate Similarity	NPC215481
0.75	Intermediate Similarity	NPC279537
0.7439	Intermediate Similarity	NPC474045
0.7439	Intermediate Similarity	NPC261253
0.7436	Intermediate Similarity	NPC308038
0.7436	Intermediate Similarity	NPC181195
0.7436	Intermediate Similarity	NPC261125
0.7436	Intermediate Similarity	NPC7232
0.7412	Intermediate Similarity	NPC473998
0.7407	Intermediate Similarity	NPC85774
0.7407	Intermediate Similarity	NPC214043
0.7407	Intermediate Similarity	NPC321187
0.7407	Intermediate Similarity	NPC161423
0.7407	Intermediate Similarity	NPC227064
0.7407	Intermediate Similarity	NPC58841
0.7407	Intermediate Similarity	NPC473246
0.7407	Intermediate Similarity	NPC329043
0.7397	Intermediate Similarity	NPC139397
0.7391	Intermediate Similarity	NPC213152
0.7381	Intermediate Similarity	NPC123912
0.7381	Intermediate Similarity	NPC473999
0.7381	Intermediate Similarity	NPC170775
0.7381	Intermediate Similarity	NPC309603
0.7375	Intermediate Similarity	NPC279186
0.7375	Intermediate Similarity	NPC256750
0.7375	Intermediate Similarity	NPC20262
0.7375	Intermediate Similarity	NPC145963
0.7368	Intermediate Similarity	NPC77501
0.7368	Intermediate Similarity	NPC114236
0.7368	Intermediate Similarity	NPC474885
0.7361	Intermediate Similarity	NPC106613
0.7361	Intermediate Similarity	NPC269985
0.7361	Intermediate Similarity	NPC475523
0.7333	Intermediate Similarity	NPC275098
0.7333	Intermediate Similarity	NPC201562
0.7333	Intermediate Similarity	NPC323437
0.7333	Intermediate Similarity	NPC29542
0.7317	Intermediate Similarity	NPC474853
0.7317	Intermediate Similarity	NPC474083
0.7317	Intermediate Similarity	NPC470574
0.7317	Intermediate Similarity	NPC179006
0.7317	Intermediate Similarity	NPC471224
0.7308	Intermediate Similarity	NPC253749
0.7308	Intermediate Similarity	NPC192006
0.7308	Intermediate Similarity	NPC474056
0.7308	Intermediate Similarity	NPC128276
0.7308	Intermediate Similarity	NPC471220
0.7308	Intermediate Similarity	NPC478122
0.7297	Intermediate Similarity	NPC2634
0.7297	Intermediate Similarity	NPC251929
0.7297	Intermediate Similarity	NPC265782
0.7297	Intermediate Similarity	NPC260040
0.7297	Intermediate Similarity	NPC307176
0.7294	Intermediate Similarity	NPC48010
0.7284	Intermediate Similarity	NPC193198
0.7284	Intermediate Similarity	NPC108045
0.7284	Intermediate Similarity	NPC41539
0.7284	Intermediate Similarity	NPC470047
0.7284	Intermediate Similarity	NPC475622
0.7284	Intermediate Similarity	NPC470046
0.7273	Intermediate Similarity	NPC27205
0.7273	Intermediate Similarity	NPC469796
0.7273	Intermediate Similarity	NPC469793
0.7273	Intermediate Similarity	NPC263582
0.726	Intermediate Similarity	NPC155198
0.7241	Intermediate Similarity	NPC8993
0.7237	Intermediate Similarity	NPC294434
0.7237	Intermediate Similarity	NPC206875
0.7237	Intermediate Similarity	NPC215050
0.7237	Intermediate Similarity	NPC15499
0.7237	Intermediate Similarity	NPC117746
0.7237	Intermediate Similarity	NPC259599
0.7231	Intermediate Similarity	NPC474141
0.7231	Intermediate Similarity	NPC296311
0.7229	Intermediate Similarity	NPC474732
0.7229	Intermediate Similarity	NPC194417
0.7229	Intermediate Similarity	NPC145879
0.7229	Intermediate Similarity	NPC222613
0.7229	Intermediate Similarity	NPC475022
0.7229	Intermediate Similarity	NPC474778
0.7229	Intermediate Similarity	NPC118648
0.7229	Intermediate Similarity	NPC474733
0.7229	Intermediate Similarity	NPC327115
0.7229	Intermediate Similarity	NPC31564
0.7215	Intermediate Similarity	NPC471299
0.7215	Intermediate Similarity	NPC19900
0.7209	Intermediate Similarity	NPC475806
0.72	Intermediate Similarity	NPC181204
0.72	Intermediate Similarity	NPC67076
0.72	Intermediate Similarity	NPC54123
0.72	Intermediate Similarity	NPC319163
0.72	Intermediate Similarity	NPC133253
0.7195	Intermediate Similarity	NPC237712
0.7195	Intermediate Similarity	NPC475100
0.7195	Intermediate Similarity	NPC238197
0.7179	Intermediate Similarity	NPC476007
0.7179	Intermediate Similarity	NPC197659
0.7179	Intermediate Similarity	NPC203403
0.7179	Intermediate Similarity	NPC74995
0.7179	Intermediate Similarity	NPC211279
0.7179	Intermediate Similarity	NPC57744
0.7176	Intermediate Similarity	NPC477215
0.7176	Intermediate Similarity	NPC476388
0.7176	Intermediate Similarity	NPC214387
0.7164	Intermediate Similarity	NPC20603
0.7162	Intermediate Similarity	NPC477448
0.7162	Intermediate Similarity	NPC10758
0.7162	Intermediate Similarity	NPC477449
0.7162	Intermediate Similarity	NPC250928
0.716	Intermediate Similarity	NPC93590
0.716	Intermediate Similarity	NPC151519
0.716	Intermediate Similarity	NPC133844
0.7143	Intermediate Similarity	NPC263698
0.7143	Intermediate Similarity	NPC136548
0.7143	Intermediate Similarity	NPC141292
0.7143	Intermediate Similarity	NPC329852
0.7143	Intermediate Similarity	NPC58063
0.7143	Intermediate Similarity	NPC317590
0.7143	Intermediate Similarity	NPC294304
0.7143	Intermediate Similarity	NPC475740
0.7143	Intermediate Similarity	NPC228574
0.7126	Intermediate Similarity	NPC472930
0.7126	Intermediate Similarity	NPC474736
0.7126	Intermediate Similarity	NPC37816
0.7126	Intermediate Similarity	NPC69454
0.7126	Intermediate Similarity	NPC109305
0.7125	Intermediate Similarity	NPC172013
0.7125	Intermediate Similarity	NPC472478
0.7125	Intermediate Similarity	NPC471514
0.7123	Intermediate Similarity	NPC477791
0.7108	Intermediate Similarity	NPC469948
0.7108	Intermediate Similarity	NPC470048
0.7108	Intermediate Similarity	NPC472931
0.7108	Intermediate Similarity	NPC476426
0.7108	Intermediate Similarity	NPC472940
0.7108	Intermediate Similarity	NPC323765
0.7105	Intermediate Similarity	NPC130016
0.7105	Intermediate Similarity	NPC303613
0.7105	Intermediate Similarity	NPC56747
0.7105	Intermediate Similarity	NPC109576
0.7105	Intermediate Similarity	NPC300940
0.7105	Intermediate Similarity	NPC474228
0.7105	Intermediate Similarity	NPC180015
0.7101	Intermediate Similarity	NPC143834
0.7101	Intermediate Similarity	NPC285594
0.7101	Intermediate Similarity	NPC96551
0.7093	Intermediate Similarity	NPC49946
0.7093	Intermediate Similarity	NPC477149
0.7093	Intermediate Similarity	NPC320026
0.7093	Intermediate Similarity	NPC477147
0.7093	Intermediate Similarity	NPC306168
0.7089	Intermediate Similarity	NPC82635

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 NPC469688 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1997
0.2-0.3	4593
0.3-0.4	1700
0.4-0.5	361
0.5-0.6	231
0.6-0.7	110
0.7-0.8	9
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
0.7763	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3133	Approved
0.7407	Intermediate Similarity	NPD3665	Phase 1
0.7407	Intermediate Similarity	NPD3666	Approved
0.7397	Intermediate Similarity	NPD4137	Phase 3
0.7297	Intermediate Similarity	NPD4747	Approved
0.7297	Intermediate Similarity	NPD4691	Approved
0.7229	Intermediate Similarity	NPD5279	Phase 3
0.7229	Intermediate Similarity	NPD3618	Phase 1
0.72	Intermediate Similarity	NPD5276	Approved
0.716	Intermediate Similarity	NPD3667	Approved
0.7108	Intermediate Similarity	NPD5363	Approved
0.7093	Intermediate Similarity	NPD5785	Approved
0.7024	Intermediate Similarity	NPD7521	Approved
0.7024	Intermediate Similarity	NPD7334	Approved
0.7024	Intermediate Similarity	NPD5330	Approved
0.7024	Intermediate Similarity	NPD6409	Approved
0.7024	Intermediate Similarity	NPD6684	Approved
0.7024	Intermediate Similarity	NPD7146	Approved
0.7013	Intermediate Similarity	NPD5733	Approved
0.7013	Intermediate Similarity	NPD4058	Approved
0.7013	Intermediate Similarity	NPD4687	Approved
0.6988	Remote Similarity	NPD4786	Approved
0.6988	Remote Similarity	NPD3668	Phase 3
0.6977	Remote Similarity	NPD5328	Approved
0.6951	Remote Similarity	NPD4269	Approved
0.6951	Remote Similarity	NPD4270	Approved
0.6951	Remote Similarity	NPD4221	Approved
0.6951	Remote Similarity	NPD4223	Phase 3
0.6951	Remote Similarity	NPD5209	Approved
0.6914	Remote Similarity	NPD4252	Approved
0.6867	Remote Similarity	NPD5362	Discontinued
0.686	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6903	Approved
0.6818	Remote Similarity	NPD6079	Approved
0.68	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4197	Approved
0.6782	Remote Similarity	NPD4753	Phase 2
0.6757	Remote Similarity	NPD7331	Phase 2
0.6747	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4202	Approved
0.6714	Remote Similarity	NPD287	Approved
0.6707	Remote Similarity	NPD4820	Approved
0.6707	Remote Similarity	NPD4821	Approved
0.6707	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4819	Approved
0.6707	Remote Similarity	NPD5368	Approved
0.6707	Remote Similarity	NPD4822	Approved
0.6706	Remote Similarity	NPD5329	Approved
0.6706	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6628	Remote Similarity	NPD4138	Approved
0.6628	Remote Similarity	NPD4519	Discontinued
0.6628	Remote Similarity	NPD5205	Approved
0.6628	Remote Similarity	NPD4689	Approved
0.6628	Remote Similarity	NPD5280	Approved
0.6628	Remote Similarity	NPD4693	Phase 3
0.6628	Remote Similarity	NPD4694	Approved
0.6628	Remote Similarity	NPD4690	Approved
0.6628	Remote Similarity	NPD5690	Phase 2
0.6628	Remote Similarity	NPD4623	Approved
0.6628	Remote Similarity	NPD5786	Approved
0.6628	Remote Similarity	NPD4688	Approved
0.6627	Remote Similarity	NPD5369	Approved
0.6627	Remote Similarity	NPD4790	Discontinued
0.6622	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6435	Approved
0.6522	Remote Similarity	NPD5221	Approved
0.6522	Remote Similarity	NPD4697	Phase 3
0.6522	Remote Similarity	NPD5222	Approved
0.6522	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4695	Discontinued
0.6494	Remote Similarity	NPD6923	Approved
0.6494	Remote Similarity	NPD6922	Approved
0.6477	Remote Similarity	NPD4518	Approved
0.6471	Remote Similarity	NPD7154	Phase 3
0.6452	Remote Similarity	NPD5173	Approved
0.6452	Remote Similarity	NPD4755	Approved
0.6437	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5695	Phase 3
0.6413	Remote Similarity	NPD5210	Approved
0.6413	Remote Similarity	NPD4629	Approved
0.641	Remote Similarity	NPD7143	Approved
0.641	Remote Similarity	NPD7144	Approved
0.64	Remote Similarity	NPD7341	Phase 2
0.6386	Remote Similarity	NPD4195	Approved
0.6383	Remote Similarity	NPD7638	Approved
0.6375	Remote Similarity	NPD6926	Approved
0.6375	Remote Similarity	NPD6924	Approved
0.6374	Remote Similarity	NPD6399	Phase 3
0.6354	Remote Similarity	NPD5211	Phase 2
0.6341	Remote Similarity	NPD5776	Phase 2
0.6341	Remote Similarity	NPD6925	Approved
0.6333	Remote Similarity	NPD4096	Approved
0.6329	Remote Similarity	NPD7151	Approved
0.6329	Remote Similarity	NPD7152	Approved
0.6329	Remote Similarity	NPD7150	Approved
0.6322	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD1696	Phase 3
0.6316	Remote Similarity	NPD4700	Approved
0.6316	Remote Similarity	NPD4696	Approved
0.6316	Remote Similarity	NPD7640	Approved
0.6316	Remote Similarity	NPD5285	Approved
0.6316	Remote Similarity	NPD7639	Approved
0.6316	Remote Similarity	NPD5286	Approved
0.631	Remote Similarity	NPD7514	Phase 3
0.6304	Remote Similarity	NPD5282	Discontinued
0.6296	Remote Similarity	NPD8039	Approved
0.6292	Remote Similarity	NPD5208	Approved
0.6279	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4788	Approved
0.6277	Remote Similarity	NPD6084	Phase 2
0.6277	Remote Similarity	NPD6083	Phase 2
0.6265	Remote Similarity	NPD7145	Approved
0.6265	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5281	Approved
0.6264	Remote Similarity	NPD5693	Phase 1
0.6264	Remote Similarity	NPD7515	Phase 2
0.6264	Remote Similarity	NPD5284	Approved
0.6264	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD5223	Approved
0.6237	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6902	Approved
0.6224	Remote Similarity	NPD5141	Approved
0.6222	Remote Similarity	NPD6904	Approved
0.6222	Remote Similarity	NPD6673	Approved
0.6222	Remote Similarity	NPD6080	Approved
0.622	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6933	Approved
0.6216	Remote Similarity	NPD4194	Approved
0.6216	Remote Similarity	NPD4193	Approved
0.6216	Remote Similarity	NPD368	Approved
0.6216	Remote Similarity	NPD4192	Approved
0.6216	Remote Similarity	NPD4191	Approved
0.6211	Remote Similarity	NPD5696	Approved
0.619	Remote Similarity	NPD6929	Approved
0.6186	Remote Similarity	NPD5224	Approved
0.6186	Remote Similarity	NPD5225	Approved
0.6186	Remote Similarity	NPD5226	Approved
0.6186	Remote Similarity	NPD4633	Approved
0.6154	Remote Similarity	NPD5207	Approved
0.6154	Remote Similarity	NPD5692	Phase 3
0.6145	Remote Similarity	NPD6932	Approved
0.6129	Remote Similarity	NPD7748	Approved
0.6122	Remote Similarity	NPD5175	Approved
0.6122	Remote Similarity	NPD5174	Approved
0.6122	Remote Similarity	NPD4754	Approved
0.6118	Remote Similarity	NPD6931	Approved
0.6118	Remote Similarity	NPD6930	Phase 2
0.6118	Remote Similarity	NPD7332	Phase 2
0.6098	Remote Similarity	NPD8264	Approved
0.6098	Remote Similarity	NPD6942	Approved
0.6098	Remote Similarity	NPD7339	Approved
0.6092	Remote Similarity	NPD6110	Phase 1
0.6087	Remote Similarity	NPD5694	Approved
0.6087	Remote Similarity	NPD6050	Approved
0.6067	Remote Similarity	NPD4249	Approved
0.6067	Remote Similarity	NPD6098	Approved
0.6064	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4139	Approved
0.6047	Remote Similarity	NPD4692	Approved
0.6023	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5133	Approved
0.6	Remote Similarity	NPD6683	Phase 2
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD4250	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD4251	Approved
0.5978	Remote Similarity	NPD46	Approved
0.5978	Remote Similarity	NPD6698	Approved
0.5977	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD4219	Approved
0.5957	Remote Similarity	NPD6001	Approved
0.5957	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7900	Approved
0.5955	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6412	Phase 2
0.5941	Remote Similarity	NPD5697	Approved
0.5941	Remote Similarity	NPD5701	Approved
0.5938	Remote Similarity	NPD7902	Approved
0.593	Remote Similarity	NPD7525	Registered
0.5921	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6695	Phase 3
0.5897	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD4730	Approved
0.5882	Remote Similarity	NPD7320	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