NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	278.135
LogP:	1.875
LogD:	1.92
LogS:	-2.565
# Rotatable Bonds:	2
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.615
Synthetic Accessibility Score:	4.759
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.44
MDCK Permeability:	2.393563772784546e-05
Pgp-inhibitor:	0.537
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.45
30% Bioavailability (F30%):	0.659

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.361
Plasma Protein Binding (PPB):	77.72200775146484%
Volume Distribution (VD):	1.206
Pgp-substrate:	29.179126739501953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.525
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.171
CYP3A4-substrate:	0.534

ADMET: Excretion

Clearance (CL):	7.391
Half-life (T1/2):	0.456

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.698
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.903
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.943
Carcinogencity:	0.727
Eye Corrosion:	0.151
Eye Irritation:	0.365
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC279186

Natural Product ID:	NPC279186
*Common Name:**	Okundoperoxide
IUPAC Name:	(3R,4aS,8aS)-3-[(E)-4-hydroxybut-2-en-2-yl]-5,5,8a-trimethyl-4,4a-dihydro-3H-1,2-benzodioxin-6-one
Synonyms:	Okundoperoxide
Standard InCHIKey:	NUNJRUBEEMMTJA-JBTZHDNBSA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-10(6-8-16)11-9-12-14(2,3)13(17)5-7-15(12,4)19-18-11/h5-7,11-12,16H,8-9H2,1-4H3/b10-6+/t11-,12+,15+/m1/s1
SMILES:	OC/C=C(/[C@@H]1OO[C@@]2([C@@H](C1)C(C)(C)C(=O)C=C2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL570305
PubChem CID:	25227596
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO32806	scleria striatinux	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19199815]

☑ 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
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.47	ug.mL-1	PMID[508084]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.483	ug.mL-1	PMID[508084]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	1.498	ug.mL-1	PMID[508084]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.308	ug.mL-1	PMID[508084]
NPT27	Others	Unspecified		IC50	=	22.7	ug.mL-1	PMID[508084]

☑ 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 NPC279186 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	165
0.1-0.2	1097
0.2-0.3	5214
0.3-0.4	12224
0.4-0.5	12442
0.5-0.6	7173
0.6-0.7	3755
0.7-0.8	600
0.8-0.85	26
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8395	Intermediate Similarity	NPC19900
0.8235	Intermediate Similarity	NPC476426
0.8182	Intermediate Similarity	NPC128672
0.8182	Intermediate Similarity	NPC134321
0.8118	Intermediate Similarity	NPC230527
0.8118	Intermediate Similarity	NPC7927
0.8095	Intermediate Similarity	NPC158411
0.8095	Intermediate Similarity	NPC38796
0.8049	Intermediate Similarity	NPC62336
0.8049	Intermediate Similarity	NPC475994
0.7978	Intermediate Similarity	NPC230332
0.7952	Intermediate Similarity	NPC308038
0.7912	Intermediate Similarity	NPC475572
0.7912	Intermediate Similarity	NPC196227
0.7907	Intermediate Similarity	NPC476412
0.7889	Intermediate Similarity	NPC172101
0.7889	Intermediate Similarity	NPC472978
0.7875	Intermediate Similarity	NPC323437
0.7875	Intermediate Similarity	NPC29542
0.7875	Intermediate Similarity	NPC201562
0.7875	Intermediate Similarity	NPC186042
0.7865	Intermediate Similarity	NPC472973
0.7865	Intermediate Similarity	NPC123912
0.7857	Intermediate Similarity	NPC172013
0.7816	Intermediate Similarity	NPC28887
0.7805	Intermediate Similarity	NPC469646
0.7805	Intermediate Similarity	NPC263582
0.7791	Intermediate Similarity	NPC105173
0.7778	Intermediate Similarity	NPC215050
0.7765	Intermediate Similarity	NPC226068
0.7727	Intermediate Similarity	NPC194417
0.7727	Intermediate Similarity	NPC472974
0.7722	Intermediate Similarity	NPC250928
0.7722	Intermediate Similarity	NPC10758
0.7717	Intermediate Similarity	NPC472976
0.7717	Intermediate Similarity	NPC472977
0.7711	Intermediate Similarity	NPC74995
0.7711	Intermediate Similarity	NPC203403
0.7701	Intermediate Similarity	NPC472326
0.7701	Intermediate Similarity	NPC40687
0.7692	Intermediate Similarity	NPC116726
0.7692	Intermediate Similarity	NPC106613
0.7692	Intermediate Similarity	NPC475441
0.7683	Intermediate Similarity	NPC474011
0.7674	Intermediate Similarity	NPC93590
0.7667	Intermediate Similarity	NPC472983
0.7647	Intermediate Similarity	NPC471514
0.7647	Intermediate Similarity	NPC470945
0.7647	Intermediate Similarity	NPC470946
0.7647	Intermediate Similarity	NPC470947
0.7634	Intermediate Similarity	NPC476245
0.7629	Intermediate Similarity	NPC473624
0.7619	Intermediate Similarity	NPC478122
0.7619	Intermediate Similarity	NPC231739
0.7609	Intermediate Similarity	NPC476416
0.7604	Intermediate Similarity	NPC224720
0.7604	Intermediate Similarity	NPC476240
0.7604	Intermediate Similarity	NPC476223
0.7595	Intermediate Similarity	NPC117804
0.759	Intermediate Similarity	NPC470525
0.7586	Intermediate Similarity	NPC64600
0.7556	Intermediate Similarity	NPC471791
0.7556	Intermediate Similarity	NPC471793
0.7553	Intermediate Similarity	NPC249954
0.7551	Intermediate Similarity	NPC118911
0.7529	Intermediate Similarity	NPC152061
0.7529	Intermediate Similarity	NPC281138
0.7529	Intermediate Similarity	NPC136033
0.7528	Intermediate Similarity	NPC476982
0.7527	Intermediate Similarity	NPC8993
0.7526	Intermediate Similarity	NPC87351
0.75	Intermediate Similarity	NPC136473
0.75	Intermediate Similarity	NPC470812
0.75	Intermediate Similarity	NPC476274
0.75	Intermediate Similarity	NPC471061
0.75	Intermediate Similarity	NPC472975
0.75	Intermediate Similarity	NPC197659
0.75	Intermediate Similarity	NPC219966
0.7474	Intermediate Similarity	NPC170131
0.7471	Intermediate Similarity	NPC145963
0.747	Intermediate Similarity	NPC114236
0.747	Intermediate Similarity	NPC216791
0.7468	Intermediate Similarity	NPC269985
0.7449	Intermediate Similarity	NPC270046
0.7449	Intermediate Similarity	NPC311612
0.7449	Intermediate Similarity	NPC111323
0.7447	Intermediate Similarity	NPC259286
0.7447	Intermediate Similarity	NPC272617
0.7447	Intermediate Similarity	NPC316215
0.7444	Intermediate Similarity	NPC287079
0.7442	Intermediate Similarity	NPC157895
0.7442	Intermediate Similarity	NPC271104
0.7442	Intermediate Similarity	NPC104120
0.7442	Intermediate Similarity	NPC148685
0.7442	Intermediate Similarity	NPC45495
0.7439	Intermediate Similarity	NPC275098
0.7423	Intermediate Similarity	NPC115862
0.7419	Intermediate Similarity	NPC474807
0.7419	Intermediate Similarity	NPC125180
0.7419	Intermediate Similarity	NPC472930
0.7416	Intermediate Similarity	NPC255174
0.7412	Intermediate Similarity	NPC275494
0.7412	Intermediate Similarity	NPC192006
0.7412	Intermediate Similarity	NPC471409
0.7391	Intermediate Similarity	NPC265856
0.7386	Intermediate Similarity	NPC476983
0.7386	Intermediate Similarity	NPC477784
0.7386	Intermediate Similarity	NPC477786
0.7386	Intermediate Similarity	NPC297398
0.7386	Intermediate Similarity	NPC477785
0.7381	Intermediate Similarity	NPC151622
0.7381	Intermediate Similarity	NPC7629
0.7375	Intermediate Similarity	NPC469688
0.7368	Intermediate Similarity	NPC471463
0.7363	Intermediate Similarity	NPC158778
0.7363	Intermediate Similarity	NPC474854
0.7356	Intermediate Similarity	NPC116797
0.7356	Intermediate Similarity	NPC470298
0.7356	Intermediate Similarity	NPC6663
0.7349	Intermediate Similarity	NPC144995
0.7349	Intermediate Similarity	NPC227814
0.734	Intermediate Similarity	NPC476415
0.734	Intermediate Similarity	NPC473162
0.734	Intermediate Similarity	NPC78159
0.734	Intermediate Similarity	NPC299100
0.734	Intermediate Similarity	NPC478089
0.734	Intermediate Similarity	NPC103527
0.7333	Intermediate Similarity	NPC234038
0.7333	Intermediate Similarity	NPC183736
0.7333	Intermediate Similarity	NPC472985
0.7333	Intermediate Similarity	NPC472986
0.7326	Intermediate Similarity	NPC7232
0.7326	Intermediate Similarity	NPC113363
0.732	Intermediate Similarity	NPC287833
0.7317	Intermediate Similarity	NPC95863
0.7312	Intermediate Similarity	NPC475806
0.7312	Intermediate Similarity	NPC473998
0.7312	Intermediate Similarity	NPC252433
0.7303	Intermediate Similarity	NPC70424
0.7303	Intermediate Similarity	NPC243618
0.7303	Intermediate Similarity	NPC227132
0.7294	Intermediate Similarity	NPC476007
0.7294	Intermediate Similarity	NPC325946
0.7294	Intermediate Similarity	NPC276769
0.7294	Intermediate Similarity	NPC97377
0.7294	Intermediate Similarity	NPC257666
0.7294	Intermediate Similarity	NPC34110
0.7294	Intermediate Similarity	NPC86917
0.7294	Intermediate Similarity	NPC266193
0.7292	Intermediate Similarity	NPC474343
0.7292	Intermediate Similarity	NPC161147
0.7284	Intermediate Similarity	NPC469914
0.7283	Intermediate Similarity	NPC212598
0.7283	Intermediate Similarity	NPC473100
0.7273	Intermediate Similarity	NPC70479
0.7273	Intermediate Similarity	NPC123505
0.7273	Intermediate Similarity	NPC103486
0.7273	Intermediate Similarity	NPC269737
0.7263	Intermediate Similarity	NPC472932
0.7263	Intermediate Similarity	NPC180950
0.7263	Intermediate Similarity	NPC214694
0.7263	Intermediate Similarity	NPC134067
0.7263	Intermediate Similarity	NPC91408
0.7262	Intermediate Similarity	NPC476346
0.7262	Intermediate Similarity	NPC472256
0.7262	Intermediate Similarity	NPC474885
0.7253	Intermediate Similarity	NPC476409
0.7253	Intermediate Similarity	NPC471792
0.7253	Intermediate Similarity	NPC472324
0.7245	Intermediate Similarity	NPC472637
0.7245	Intermediate Similarity	NPC81530
0.7245	Intermediate Similarity	NPC470184
0.7241	Intermediate Similarity	NPC472301
0.7241	Intermediate Similarity	NPC306095
0.7234	Intermediate Similarity	NPC474736
0.7234	Intermediate Similarity	NPC69454
0.7229	Intermediate Similarity	NPC153660
0.7229	Intermediate Similarity	NPC247586
0.7228	Intermediate Similarity	NPC185
0.7222	Intermediate Similarity	NPC179006
0.7222	Intermediate Similarity	NPC36350
0.7222	Intermediate Similarity	NPC474853
0.7222	Intermediate Similarity	NPC15807
0.7222	Intermediate Similarity	NPC70685
0.7222	Intermediate Similarity	NPC471344
0.7216	Intermediate Similarity	NPC141191
0.7216	Intermediate Similarity	NPC197386
0.7216	Intermediate Similarity	NPC23364
0.7216	Intermediate Similarity	NPC316598
0.7209	Intermediate Similarity	NPC121200
0.7204	Intermediate Similarity	NPC473455
0.7204	Intermediate Similarity	NPC166554
0.7204	Intermediate Similarity	NPC214844
0.7204	Intermediate Similarity	NPC320026
0.7204	Intermediate Similarity	NPC473099
0.72	Intermediate Similarity	NPC309190
0.7191	Intermediate Similarity	NPC110150
0.7191	Intermediate Similarity	NPC49019
0.7191	Intermediate Similarity	NPC66764
0.7191	Intermediate Similarity	NPC251475

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 NPC279186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1459
0.2-0.3	3991
0.3-0.4	2469
0.4-0.5	676
0.5-0.6	221
0.6-0.7	175
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
0.7347	Intermediate Similarity	NPD5211	Phase 2
0.7209	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD5286	Approved
0.7143	Intermediate Similarity	NPD5285	Approved
0.7128	Intermediate Similarity	NPD6079	Approved
0.7125	Intermediate Similarity	NPD7331	Phase 2
0.7083	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5223	Approved
0.7033	Intermediate Similarity	NPD5363	Approved
0.7033	Intermediate Similarity	NPD1694	Approved
0.7021	Intermediate Similarity	NPD5785	Approved
0.701	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5221	Approved
0.701	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5226	Approved
0.7	Intermediate Similarity	NPD4633	Approved
0.7	Intermediate Similarity	NPD5225	Approved
0.7	Intermediate Similarity	NPD5224	Approved
0.6957	Remote Similarity	NPD4519	Discontinued
0.6957	Remote Similarity	NPD3618	Phase 1
0.6957	Remote Similarity	NPD4623	Approved
0.6939	Remote Similarity	NPD4755	Approved
0.6939	Remote Similarity	NPD5173	Approved
0.6931	Remote Similarity	NPD5175	Approved
0.6931	Remote Similarity	NPD5174	Approved
0.6923	Remote Similarity	NPD3133	Approved
0.6923	Remote Similarity	NPD3666	Approved
0.6923	Remote Similarity	NPD3665	Phase 1
0.6915	Remote Similarity	NPD5328	Approved
0.6907	Remote Similarity	NPD5210	Approved
0.6907	Remote Similarity	NPD4629	Approved
0.6854	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4695	Discontinued
0.6848	Remote Similarity	NPD1696	Phase 3
0.6837	Remote Similarity	NPD4697	Phase 3
0.6835	Remote Similarity	NPD368	Approved
0.6804	Remote Similarity	NPD5282	Discontinued
0.68	Remote Similarity	NPD4700	Approved
0.679	Remote Similarity	NPD7341	Phase 2
0.6774	Remote Similarity	NPD5279	Phase 3
0.6774	Remote Similarity	NPD5786	Approved
0.6771	Remote Similarity	NPD6411	Approved
0.6737	Remote Similarity	NPD4753	Phase 2
0.6731	Remote Similarity	NPD5697	Approved
0.6703	Remote Similarity	NPD4269	Approved
0.6703	Remote Similarity	NPD3667	Approved
0.6703	Remote Similarity	NPD4270	Approved
0.6702	Remote Similarity	NPD3573	Approved
0.6701	Remote Similarity	NPD4202	Approved
0.6701	Remote Similarity	NPD5779	Approved
0.6701	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.6636	Remote Similarity	NPD6649	Approved
0.6636	Remote Similarity	NPD6650	Approved
0.663	Remote Similarity	NPD6110	Phase 1
0.6604	Remote Similarity	NPD6014	Approved
0.6604	Remote Similarity	NPD6013	Approved
0.6604	Remote Similarity	NPD6012	Approved
0.6602	Remote Similarity	NPD4754	Approved
0.6598	Remote Similarity	NPD7515	Phase 2
0.6598	Remote Similarity	NPD5284	Approved
0.6598	Remote Similarity	NPD5281	Approved
0.6596	Remote Similarity	NPD5690	Phase 2
0.6596	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6101	Approved
0.6562	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4786	Approved
0.6542	Remote Similarity	NPD4634	Approved
0.6542	Remote Similarity	NPD5251	Approved
0.6542	Remote Similarity	NPD6883	Approved
0.6542	Remote Similarity	NPD7102	Approved
0.6542	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5249	Phase 3
0.6542	Remote Similarity	NPD5135	Approved
0.6542	Remote Similarity	NPD7290	Approved
0.6542	Remote Similarity	NPD5169	Approved
0.6542	Remote Similarity	NPD5248	Approved
0.6542	Remote Similarity	NPD5250	Approved
0.6542	Remote Similarity	NPD5247	Approved
0.6522	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4221	Approved
0.6522	Remote Similarity	NPD6435	Approved
0.6522	Remote Similarity	NPD4223	Phase 3
0.6509	Remote Similarity	NPD5128	Approved
0.6484	Remote Similarity	NPD4820	Approved
0.6484	Remote Similarity	NPD4821	Approved
0.6484	Remote Similarity	NPD4819	Approved
0.6484	Remote Similarity	NPD4822	Approved
0.6481	Remote Similarity	NPD6617	Approved
0.6481	Remote Similarity	NPD5215	Approved
0.6481	Remote Similarity	NPD5127	Approved
0.6481	Remote Similarity	NPD5216	Approved
0.6481	Remote Similarity	NPD5217	Approved
0.6481	Remote Similarity	NPD8130	Phase 1
0.6481	Remote Similarity	NPD6847	Approved
0.6481	Remote Similarity	NPD6869	Approved
0.6477	Remote Similarity	NPD8264	Approved
0.6476	Remote Similarity	NPD5739	Approved
0.6476	Remote Similarity	NPD7128	Approved
0.6476	Remote Similarity	NPD4767	Approved
0.6476	Remote Similarity	NPD6675	Approved
0.6476	Remote Similarity	NPD6402	Approved
0.6476	Remote Similarity	NPD4768	Approved
0.6452	Remote Similarity	NPD5362	Discontinued
0.6449	Remote Similarity	NPD6372	Approved
0.6449	Remote Similarity	NPD6373	Approved
0.6436	Remote Similarity	NPD7902	Approved
0.6422	Remote Similarity	NPD8297	Approved
0.6422	Remote Similarity	NPD6882	Approved
0.6415	Remote Similarity	NPD5701	Approved
0.6413	Remote Similarity	NPD5369	Approved
0.6395	Remote Similarity	NPD4691	Approved
0.6383	Remote Similarity	NPD3668	Phase 3
0.6383	Remote Similarity	NPD4197	Approved
0.6373	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4058	Approved
0.6364	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD6399	Phase 3
0.6355	Remote Similarity	NPD7320	Approved
0.6355	Remote Similarity	NPD5168	Approved
0.6344	Remote Similarity	NPD5209	Approved
0.6339	Remote Similarity	NPD7115	Discovery
0.6327	Remote Similarity	NPD6698	Approved
0.6327	Remote Similarity	NPD46	Approved
0.6316	Remote Similarity	NPD5329	Approved
0.6306	Remote Similarity	NPD5167	Approved
0.63	Remote Similarity	NPD7748	Approved
0.63	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7900	Approved
0.6289	Remote Similarity	NPD4518	Approved
0.6279	Remote Similarity	NPD4137	Phase 3
0.6277	Remote Similarity	NPD7154	Phase 3
0.6275	Remote Similarity	NPD6084	Phase 2
0.6275	Remote Similarity	NPD6083	Phase 2
0.6264	Remote Similarity	NPD4271	Approved
0.6264	Remote Similarity	NPD4268	Approved
0.6264	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7983	Approved
0.625	Remote Similarity	NPD7334	Approved
0.625	Remote Similarity	NPD4138	Approved
0.625	Remote Similarity	NPD5280	Approved
0.625	Remote Similarity	NPD6409	Approved
0.625	Remote Similarity	NPD5205	Approved
0.625	Remote Similarity	NPD5330	Approved
0.625	Remote Similarity	NPD4689	Approved
0.625	Remote Similarity	NPD7521	Approved
0.625	Remote Similarity	NPD7146	Approved
0.625	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD4690	Approved
0.625	Remote Similarity	NPD4688	Approved
0.625	Remote Similarity	NPD4693	Phase 3
0.625	Remote Similarity	NPD4694	Approved
0.6239	Remote Similarity	NPD6371	Approved
0.6238	Remote Similarity	NPD5695	Phase 3
0.6214	Remote Similarity	NPD4225	Approved
0.6214	Remote Similarity	NPD5696	Approved
0.6207	Remote Similarity	NPD4747	Approved
0.6204	Remote Similarity	NPD6686	Approved
0.6196	Remote Similarity	NPD4195	Approved
0.6195	Remote Similarity	NPD6317	Approved
0.6195	Remote Similarity	NPD6009	Approved
0.6182	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4687	Approved
0.6176	Remote Similarity	NPD7839	Suspended
0.617	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6008	Approved
0.6154	Remote Similarity	NPD4756	Discovery
0.6145	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6313	Approved
0.614	Remote Similarity	NPD6335	Approved
0.614	Remote Similarity	NPD6314	Approved
0.6136	Remote Similarity	NPD5276	Approved
0.6129	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7332	Phase 2
0.6129	Remote Similarity	NPD7514	Phase 3
0.6122	Remote Similarity	NPD6903	Approved
0.6122	Remote Similarity	NPD5737	Approved
0.6122	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6672	Approved
0.6121	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6412	Phase 2
0.6111	Remote Similarity	NPD8039	Approved
0.6106	Remote Similarity	NPD6274	Approved
0.6105	Remote Similarity	NPD4788	Approved
0.6105	Remote Similarity	NPD5332	Approved
0.6105	Remote Similarity	NPD5331	Approved
0.61	Remote Similarity	NPD7637	Suspended
0.6087	Remote Similarity	NPD7101	Approved
0.6087	Remote Similarity	NPD7100	Approved
0.6087	Remote Similarity	NPD3617	Approved
0.6064	Remote Similarity	NPD4790	Discontinued
0.6049	Remote Similarity	NPD287	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