NPASS Compound

Structure

CID275494 OpenBabel06191716082D 22 23 0 0 1 0 0 0 0 0999 V2000 1.7424 3.1566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7765 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9239 0.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7765 2.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5176 1.9319 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4836 1.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 18 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 20 1 6 0 0 0 15 19 1 0 0 0 0 16 21 2 0 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 18 22 1 0 0 0 0 19 5 1 6 0 0 0 20 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	347.034
LogP:	3.483
LogD:	3.205
LogS:	-4.288
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.766
Synthetic Accessibility Score:	4.591
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.804
MDCK Permeability:	1.999618689296767e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	91.84607696533203%
Volume Distribution (VD):	0.769
Pgp-substrate:	10.301567077636719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.732
CYP2C19-inhibitor:	0.285
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.172
CYP2C9-substrate:	0.177
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.205
CYP3A4-inhibitor:	0.858
CYP3A4-substrate:	0.791

ADMET: Excretion

Clearance (CL):	5.816
Half-life (T1/2):	0.653

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.239
Skin Sensitization:	0.944
Carcinogencity:	0.106
Eye Corrosion:	0.759
Eye Irritation:	0.894
Respiratory Toxicity:	0.895

Download Data

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

Natural Product: NPC275494

Natural Product ID:	NPC275494
*Common Name:**	Roseostachenone
IUPAC Name:	(4aR,7R,8S,8aR)-8-(3-hydroxy-3-methylpent-4-enyl)-4,4a,7,8-tetramethyl-5,6,7,8a-tetrahydro-1H-naphthalen-2-one
Synonyms:
Standard InCHIKey:	KARUSPOBGJZEMI-INTGFUSFSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-7-18(4,22)10-11-20(6)14(2)8-9-19(5)15(3)12-16(21)13-17(19)20/h7,12,14,17,22H,1,8-11,13H2,2-6H3/t14-,17+,18?,19+,20+/m1/s1
SMILES:	C=CC(CC[C@@]1(C)[C@H](C)CC[C@@]2([C@@H]1CC(=O)C=C2C)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3394775
PubChem CID:	10542571
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO33595	Stachys glutinosa	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25562563]
NPO8496	Aristolochia chamissonis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8496	Aristolochia chamissonis	Species	Aristolochiaceae	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
Ki	2
Others	1

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1168	Individual Protein	Mu opioid receptor	Mus musculus	Ki	=	40500.0	nM	PMID[488865]
NPT1167	Individual Protein	Delta opioid receptor	Mus musculus	Ki	=	23500.0	nM	PMID[488865]
NPT2	Others	Unspecified		Ratio Ki	=	0.58	n.a.	PMID[488865]

☑ 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 NPC275494 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	158
0.1-0.2	1127
0.2-0.3	5253
0.3-0.4	14287
0.4-0.5	10309
0.5-0.6	6594
0.6-0.7	3648
0.7-0.8	1138
0.8-0.85	144
0.85-0.9	31
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471409
0.9324	High Similarity	NPC266193
0.9324	High Similarity	NPC257666
0.92	High Similarity	NPC179028
0.8961	High Similarity	NPC476809
0.8933	High Similarity	NPC263582
0.8933	High Similarity	NPC472305
0.8816	High Similarity	NPC97377
0.8816	High Similarity	NPC34110
0.8784	High Similarity	NPC247586
0.875	High Similarity	NPC476412
0.8718	High Similarity	NPC2482
0.8701	High Similarity	NPC62336
0.8684	High Similarity	NPC151622
0.8684	High Similarity	NPC7629
0.8684	High Similarity	NPC180886
0.8675	High Similarity	NPC262043
0.8659	High Similarity	NPC136948
0.8649	High Similarity	NPC84790
0.8608	High Similarity	NPC473217
0.8608	High Similarity	NPC472684
0.8608	High Similarity	NPC477372
0.8608	High Similarity	NPC278459
0.8608	High Similarity	NPC226068
0.8608	High Similarity	NPC471898
0.8608	High Similarity	NPC44963
0.859	High Similarity	NPC308038
0.859	High Similarity	NPC170394
0.8571	High Similarity	NPC165711
0.8553	High Similarity	NPC476795
0.8537	High Similarity	NPC194417
0.85	High Similarity	NPC193347
0.8481	Intermediate Similarity	NPC469637
0.8481	Intermediate Similarity	NPC108955
0.8481	Intermediate Similarity	NPC172013
0.8472	Intermediate Similarity	NPC279434
0.8471	Intermediate Similarity	NPC204341
0.8471	Intermediate Similarity	NPC475806
0.8462	Intermediate Similarity	NPC321514
0.8462	Intermediate Similarity	NPC74410
0.8462	Intermediate Similarity	NPC297996
0.8462	Intermediate Similarity	NPC189485
0.8452	Intermediate Similarity	NPC36668
0.8452	Intermediate Similarity	NPC118011
0.8442	Intermediate Similarity	NPC186554
0.8442	Intermediate Similarity	NPC76966
0.8434	Intermediate Similarity	NPC476409
0.8434	Intermediate Similarity	NPC471792
0.8421	Intermediate Similarity	NPC18819
0.8421	Intermediate Similarity	NPC46610
0.8415	Intermediate Similarity	NPC476426
0.8415	Intermediate Similarity	NPC469993
0.8415	Intermediate Similarity	NPC474537
0.8415	Intermediate Similarity	NPC29447
0.84	Intermediate Similarity	NPC160817
0.8395	Intermediate Similarity	NPC49019
0.8395	Intermediate Similarity	NPC53733
0.8395	Intermediate Similarity	NPC97913
0.8375	Intermediate Similarity	NPC121984
0.8375	Intermediate Similarity	NPC189237
0.8375	Intermediate Similarity	NPC55869
0.8375	Intermediate Similarity	NPC225515
0.8354	Intermediate Similarity	NPC231431
0.8354	Intermediate Similarity	NPC477371
0.8354	Intermediate Similarity	NPC215843
0.8333	Intermediate Similarity	NPC61952
0.8333	Intermediate Similarity	NPC197659
0.8333	Intermediate Similarity	NPC48107
0.8333	Intermediate Similarity	NPC325946
0.8333	Intermediate Similarity	NPC74995
0.8333	Intermediate Similarity	NPC72397
0.8313	Intermediate Similarity	NPC472974
0.8313	Intermediate Similarity	NPC472869
0.8312	Intermediate Similarity	NPC279666
0.8312	Intermediate Similarity	NPC476346
0.8312	Intermediate Similarity	NPC192540
0.8293	Intermediate Similarity	NPC251170
0.8293	Intermediate Similarity	NPC214043
0.8293	Intermediate Similarity	NPC473246
0.8293	Intermediate Similarity	NPC164577
0.8293	Intermediate Similarity	NPC472865
0.8293	Intermediate Similarity	NPC85774
0.8293	Intermediate Similarity	NPC144258
0.8293	Intermediate Similarity	NPC96095
0.8289	Intermediate Similarity	NPC180015
0.8289	Intermediate Similarity	NPC109576
0.8289	Intermediate Similarity	NPC35656
0.8289	Intermediate Similarity	NPC130016
0.8289	Intermediate Similarity	NPC56747
0.8276	Intermediate Similarity	NPC8993
0.8272	Intermediate Similarity	NPC93590
0.8272	Intermediate Similarity	NPC302661
0.8272	Intermediate Similarity	NPC238991
0.8272	Intermediate Similarity	NPC320514
0.825	Intermediate Similarity	NPC306095
0.825	Intermediate Similarity	NPC26139
0.825	Intermediate Similarity	NPC37038
0.825	Intermediate Similarity	NPC472301
0.8235	Intermediate Similarity	NPC472688
0.8235	Intermediate Similarity	NPC2983
0.8235	Intermediate Similarity	NPC309603
0.8235	Intermediate Similarity	NPC472676
0.8235	Intermediate Similarity	NPC472973
0.8235	Intermediate Similarity	NPC473999
0.8235	Intermediate Similarity	NPC472983
0.8228	Intermediate Similarity	NPC475994
0.8228	Intermediate Similarity	NPC207772
0.8228	Intermediate Similarity	NPC476808
0.8228	Intermediate Similarity	NPC198240
0.8219	Intermediate Similarity	NPC103734
0.8214	Intermediate Similarity	NPC93778
0.8214	Intermediate Similarity	NPC58063
0.8205	Intermediate Similarity	NPC470525
0.8205	Intermediate Similarity	NPC69143
0.8205	Intermediate Similarity	NPC92080
0.8193	Intermediate Similarity	NPC471224
0.8193	Intermediate Similarity	NPC474083
0.8193	Intermediate Similarity	NPC269638
0.8193	Intermediate Similarity	NPC274724
0.8193	Intermediate Similarity	NPC469948
0.8193	Intermediate Similarity	NPC33663
0.8182	Intermediate Similarity	NPC241854
0.8182	Intermediate Similarity	NPC283908
0.8182	Intermediate Similarity	NPC470299
0.8182	Intermediate Similarity	NPC259286
0.8182	Intermediate Similarity	NPC476046
0.8182	Intermediate Similarity	NPC103958
0.8182	Intermediate Similarity	NPC161923
0.8182	Intermediate Similarity	NPC183503
0.8182	Intermediate Similarity	NPC251970
0.8171	Intermediate Similarity	NPC477373
0.8171	Intermediate Similarity	NPC64600
0.8161	Intermediate Similarity	NPC474736
0.8148	Intermediate Similarity	NPC162632
0.8148	Intermediate Similarity	NPC201912
0.8148	Intermediate Similarity	NPC116797
0.8148	Intermediate Similarity	NPC147066
0.8148	Intermediate Similarity	NPC263272
0.8148	Intermediate Similarity	NPC38350
0.8148	Intermediate Similarity	NPC267691
0.8148	Intermediate Similarity	NPC3915
0.8148	Intermediate Similarity	NPC274050
0.8148	Intermediate Similarity	NPC327002
0.8148	Intermediate Similarity	NPC142244
0.814	Intermediate Similarity	NPC48010
0.8133	Intermediate Similarity	NPC469914
0.8125	Intermediate Similarity	NPC281138
0.8125	Intermediate Similarity	NPC474113
0.8125	Intermediate Similarity	NPC152061
0.8118	Intermediate Similarity	NPC471791
0.8118	Intermediate Similarity	NPC117122
0.8118	Intermediate Similarity	NPC472870
0.8118	Intermediate Similarity	NPC471793
0.8101	Intermediate Similarity	NPC472300
0.8101	Intermediate Similarity	NPC132542
0.8101	Intermediate Similarity	NPC471899
0.8101	Intermediate Similarity	NPC471897
0.8101	Intermediate Similarity	NPC107039
0.8095	Intermediate Similarity	NPC94666
0.8095	Intermediate Similarity	NPC474778
0.8095	Intermediate Similarity	NPC145879
0.8095	Intermediate Similarity	NPC472986
0.8095	Intermediate Similarity	NPC472985
0.8095	Intermediate Similarity	NPC474732
0.8095	Intermediate Similarity	NPC222613
0.8095	Intermediate Similarity	NPC118648
0.8095	Intermediate Similarity	NPC472479
0.8095	Intermediate Similarity	NPC31564
0.8095	Intermediate Similarity	NPC470955
0.8095	Intermediate Similarity	NPC469994
0.8095	Intermediate Similarity	NPC474733
0.8095	Intermediate Similarity	NPC475022
0.809	Intermediate Similarity	NPC249954
0.8077	Intermediate Similarity	NPC114236
0.8077	Intermediate Similarity	NPC476844
0.8072	Intermediate Similarity	NPC165064
0.8072	Intermediate Similarity	NPC19849
0.8072	Intermediate Similarity	NPC58841
0.8072	Intermediate Similarity	NPC161423
0.8072	Intermediate Similarity	NPC227064
0.8072	Intermediate Similarity	NPC329043
0.8072	Intermediate Similarity	NPC472864
0.8072	Intermediate Similarity	NPC237712
0.8072	Intermediate Similarity	NPC321187
0.8068	Intermediate Similarity	NPC299100
0.8052	Intermediate Similarity	NPC186042
0.8049	Intermediate Similarity	NPC133391
0.8049	Intermediate Similarity	NPC251779
0.8049	Intermediate Similarity	NPC310989
0.8049	Intermediate Similarity	NPC103486
0.8049	Intermediate Similarity	NPC260956
0.8049	Intermediate Similarity	NPC69101
0.8049	Intermediate Similarity	NPC92226
0.8046	Intermediate Similarity	NPC473986
0.8046	Intermediate Similarity	NPC472978
0.8046	Intermediate Similarity	NPC474018
0.8046	Intermediate Similarity	NPC473998
0.8025	Intermediate Similarity	NPC157895
0.8025	Intermediate Similarity	NPC104120
0.8025	Intermediate Similarity	NPC18955

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 NPC275494 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1535
0.2-0.3	3876
0.3-0.4	2428
0.4-0.5	686
0.5-0.6	227
0.6-0.7	163
0.7-0.8	70
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8765	High Similarity	NPD4623	Approved
0.8765	High Similarity	NPD4519	Discontinued
0.85	High Similarity	NPD4223	Phase 3
0.85	High Similarity	NPD4221	Approved
0.8415	Intermediate Similarity	NPD5329	Approved
0.8313	Intermediate Similarity	NPD5690	Phase 2
0.8293	Intermediate Similarity	NPD4197	Approved
0.825	Intermediate Similarity	NPD4695	Discontinued
0.8095	Intermediate Similarity	NPD4689	Approved
0.8095	Intermediate Similarity	NPD5205	Approved
0.8095	Intermediate Similarity	NPD4690	Approved
0.8095	Intermediate Similarity	NPD4693	Phase 3
0.8095	Intermediate Similarity	NPD4694	Approved
0.8095	Intermediate Similarity	NPD5280	Approved
0.8095	Intermediate Similarity	NPD4688	Approved
0.8095	Intermediate Similarity	NPD4138	Approved
0.8072	Intermediate Similarity	NPD3666	Approved
0.8072	Intermediate Similarity	NPD3133	Approved
0.8072	Intermediate Similarity	NPD3665	Phase 1
0.8	Intermediate Similarity	NPD3617	Approved
0.7973	Intermediate Similarity	NPD7331	Phase 2
0.7901	Intermediate Similarity	NPD4195	Approved
0.7882	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3618	Phase 1
0.7857	Intermediate Similarity	NPD4786	Approved
0.7841	Intermediate Similarity	NPD6079	Approved
0.7841	Intermediate Similarity	NPD5281	Approved
0.7841	Intermediate Similarity	NPD5284	Approved
0.7838	Intermediate Similarity	NPD7341	Phase 2
0.7831	Intermediate Similarity	NPD3667	Approved
0.7816	Intermediate Similarity	NPD4753	Phase 2
0.7816	Intermediate Similarity	NPD5328	Approved
0.7674	Intermediate Similarity	NPD5279	Phase 3
0.7662	Intermediate Similarity	NPD4137	Phase 3
0.764	Intermediate Similarity	NPD7515	Phase 2
0.7614	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3573	Approved
0.7582	Intermediate Similarity	NPD4629	Approved
0.7582	Intermediate Similarity	NPD5210	Approved
0.7564	Intermediate Similarity	NPD4747	Approved
0.7564	Intermediate Similarity	NPD4691	Approved
0.7556	Intermediate Similarity	NPD4202	Approved
0.7528	Intermediate Similarity	NPD4096	Approved
0.75	Intermediate Similarity	NPD4687	Approved
0.75	Intermediate Similarity	NPD4518	Approved
0.75	Intermediate Similarity	NPD4058	Approved
0.75	Intermediate Similarity	NPD4139	Approved
0.75	Intermediate Similarity	NPD4692	Approved
0.75	Intermediate Similarity	NPD5733	Approved
0.7474	Intermediate Similarity	NPD5211	Phase 2
0.7473	Intermediate Similarity	NPD7748	Approved
0.7471	Intermediate Similarity	NPD7146	Approved
0.7471	Intermediate Similarity	NPD7521	Approved
0.7471	Intermediate Similarity	NPD7334	Approved
0.7471	Intermediate Similarity	NPD6409	Approved
0.7471	Intermediate Similarity	NPD6684	Approved
0.7471	Intermediate Similarity	NPD5330	Approved
0.7419	Intermediate Similarity	NPD6083	Phase 2
0.7419	Intermediate Similarity	NPD6084	Phase 2
0.7416	Intermediate Similarity	NPD6673	Approved
0.7416	Intermediate Similarity	NPD6904	Approved
0.7416	Intermediate Similarity	NPD6080	Approved
0.7391	Intermediate Similarity	NPD5695	Phase 3
0.7363	Intermediate Similarity	NPD5133	Approved
0.7333	Intermediate Similarity	NPD5207	Approved
0.7326	Intermediate Similarity	NPD4788	Approved
0.732	Intermediate Similarity	NPD5141	Approved
0.7312	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5221	Approved
0.7312	Intermediate Similarity	NPD5222	Approved
0.7303	Intermediate Similarity	NPD5737	Approved
0.7303	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6903	Approved
0.7303	Intermediate Similarity	NPD6672	Approved
0.7303	Intermediate Similarity	NPD5208	Approved
0.7284	Intermediate Similarity	NPD4784	Approved
0.7284	Intermediate Similarity	NPD4785	Approved
0.7273	Intermediate Similarity	NPD6098	Approved
0.7263	Intermediate Similarity	NPD5286	Approved
0.7263	Intermediate Similarity	NPD4696	Approved
0.7263	Intermediate Similarity	NPD5285	Approved
0.7253	Intermediate Similarity	NPD6050	Approved
0.7253	Intermediate Similarity	NPD5694	Approved
0.7253	Intermediate Similarity	NPD5693	Phase 1
0.725	Intermediate Similarity	NPD5276	Approved
0.725	Intermediate Similarity	NPD4243	Approved
0.7241	Intermediate Similarity	NPD3668	Phase 3
0.7234	Intermediate Similarity	NPD5173	Approved
0.7234	Intermediate Similarity	NPD7902	Approved
0.7234	Intermediate Similarity	NPD4755	Approved
0.7188	Intermediate Similarity	NPD5223	Approved
0.7174	Intermediate Similarity	NPD6399	Phase 3
0.7158	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.7128	Intermediate Similarity	NPD7614	Phase 1
0.7128	Intermediate Similarity	NPD4697	Phase 3
0.7113	Intermediate Similarity	NPD5091	Approved
0.7113	Intermediate Similarity	NPD5225	Approved
0.7113	Intermediate Similarity	NPD4633	Approved
0.7113	Intermediate Similarity	NPD5224	Approved
0.7113	Intermediate Similarity	NPD5226	Approved
0.7089	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6404	Discontinued
0.7083	Intermediate Similarity	NPD4700	Approved
0.7041	Intermediate Similarity	NPD5175	Approved
0.7041	Intermediate Similarity	NPD5174	Approved
0.7027	Intermediate Similarity	NPD287	Approved
0.7021	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1696	Phase 3
0.6966	Remote Similarity	NPD1694	Approved
0.6941	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6899	Approved
0.6931	Remote Similarity	NPD6881	Approved
0.6915	Remote Similarity	NPD7900	Approved
0.6915	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6001	Approved
0.69	Remote Similarity	NPD6402	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD6675	Approved
0.6869	Remote Similarity	NPD4754	Approved
0.6832	Remote Similarity	NPD5697	Approved
0.6796	Remote Similarity	NPD7102	Approved
0.6796	Remote Similarity	NPD6883	Approved
0.6796	Remote Similarity	NPD7290	Approved
0.6786	Remote Similarity	NPD5275	Approved
0.6786	Remote Similarity	NPD4190	Phase 3
0.6786	Remote Similarity	NPD8264	Approved
0.6786	Remote Similarity	NPD7339	Approved
0.6786	Remote Similarity	NPD6942	Approved
0.6765	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD4730	Approved
0.6765	Remote Similarity	NPD6011	Approved
0.6765	Remote Similarity	NPD4729	Approved
0.6742	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7639	Approved
0.6735	Remote Similarity	NPD7640	Approved
0.6733	Remote Similarity	NPD4767	Approved
0.6733	Remote Similarity	NPD4768	Approved
0.6731	Remote Similarity	NPD6650	Approved
0.6731	Remote Similarity	NPD8130	Phase 1
0.6731	Remote Similarity	NPD6617	Approved
0.6731	Remote Similarity	NPD6869	Approved
0.6731	Remote Similarity	NPD6649	Approved
0.6731	Remote Similarity	NPD6847	Approved
0.6729	Remote Similarity	NPD7115	Discovery
0.6706	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8028	Phase 2
0.6702	Remote Similarity	NPD6411	Approved
0.6699	Remote Similarity	NPD6014	Approved
0.6699	Remote Similarity	NPD6373	Approved
0.6699	Remote Similarity	NPD6372	Approved
0.6699	Remote Similarity	NPD6012	Approved
0.6699	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD5654	Approved
0.6635	Remote Similarity	NPD5135	Approved
0.6635	Remote Similarity	NPD5250	Approved
0.6635	Remote Similarity	NPD5248	Approved
0.6635	Remote Similarity	NPD5169	Approved
0.6635	Remote Similarity	NPD5249	Phase 3
0.6635	Remote Similarity	NPD4634	Approved
0.6635	Remote Similarity	NPD5247	Approved
0.6635	Remote Similarity	NPD5251	Approved
0.6635	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7638	Approved
0.6632	Remote Similarity	NPD5779	Approved
0.6632	Remote Similarity	NPD5778	Approved
0.6602	Remote Similarity	NPD5168	Approved
0.6602	Remote Similarity	NPD5128	Approved
0.6598	Remote Similarity	NPD7732	Phase 3
0.6596	Remote Similarity	NPD5785	Approved
0.6593	Remote Similarity	NPD5363	Approved
0.6593	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6931	Approved
0.6591	Remote Similarity	NPD7525	Registered
0.6591	Remote Similarity	NPD6930	Phase 2
0.6588	Remote Similarity	NPD8039	Approved
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5217	Approved
0.6571	Remote Similarity	NPD5215	Approved
0.6571	Remote Similarity	NPD5216	Approved
0.6571	Remote Similarity	NPD5127	Approved
0.6562	Remote Similarity	NPD5282	Discontinued
0.6552	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4194	Approved
0.6538	Remote Similarity	NPD4193	Approved
0.6538	Remote Similarity	NPD4191	Approved
0.6538	Remote Similarity	NPD4192	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