NPASS Compound

Structure

NPC46880 OpenBabel07101719242D 25 27 0 0 1 0 0 0 0 0999 V2000 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7453 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7453 3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7453 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 23 1 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 24 1 0 0 0 0 11 25 1 0 0 0 0 12 1 1 1 0 0 0 12 13 1 0 0 0 0 13 2 1 6 0 0 0 13 20 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 20 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	341.348
LogP:	1.634
LogD:	1.991
LogS:	-3.217
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.731
Synthetic Accessibility Score:	5.774
Fsp3:	0.85
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:	-4.74
MDCK Permeability:	1.1645273843896575e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.258
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.461
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.833
Plasma Protein Binding (PPB):	70.27460479736328%
Volume Distribution (VD):	1.045
Pgp-substrate:	16.292055130004883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.423
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.728
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.87
CYP3A4-substrate:	0.286

ADMET: Excretion

Clearance (CL):	6.071
Half-life (T1/2):	0.744

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.663
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.782
Carcinogencity:	0.889
Eye Corrosion:	0.408
Eye Irritation:	0.53
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC46880

Natural Product ID:	NPC46880
*Common Name:**	Oleiferin D
IUPAC Name:	(2S,3R)-4-(1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one
Synonyms:	Oleiferin D
Standard InCHIKey:	UFCKYLUYWNYRRX-OLZOCXBDSA-N
Standard InCHI:	InChI=1S/C20H22O5/c1-12(8-14-4-7-17-19(9-14)25-11-24-17)13(2)20(22)15-5-6-16(21)18(10-15)23-3/h4-7,9-10,12-13,21H,8,11H2,1-3H3/t12-,13+/m1/s1
SMILES:	COc1cc(ccc1O)C(=O)[C@H]([C@@H](Cc1ccc2c(c1)OCO2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL410045
PubChem CID:	44450596
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane lignans

*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
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579855]
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18242997]
NPO2754	Iryanthera lancifolia	Species	Myristicaceae	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
Others	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	MED	=	10.0	uM	PMID[543190]
NPT83	Cell Line	MCF7	Homo sapiens	Ratio	=	4.0	n.a.	PMID[543190]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.01	%	PMID[543190]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	42.8	%	PMID[543190]

☑ 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 NPC46880 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	335
0.1-0.2	1441
0.2-0.3	3500
0.3-0.4	8933
0.4-0.5	9662
0.5-0.6	3364
0.6-0.7	7482
0.7-0.8	7395
0.8-0.85	471
0.85-0.9	99
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9779	High Similarity	NPC28398
0.9091	High Similarity	NPC327052
0.9085	High Similarity	NPC176030
0.9085	High Similarity	NPC192597
0.9085	High Similarity	NPC125134
0.9085	High Similarity	NPC169214
0.9085	High Similarity	NPC86455
0.9085	High Similarity	NPC229218
0.9085	High Similarity	NPC137920
0.9085	High Similarity	NPC141817
0.9044	High Similarity	NPC66905
0.9021	High Similarity	NPC46161
0.9021	High Similarity	NPC239608
0.8944	High Similarity	NPC282291
0.8944	High Similarity	NPC166137
0.8929	High Similarity	NPC90431
0.8881	High Similarity	NPC52664
0.8874	High Similarity	NPC474990
0.8832	High Similarity	NPC304622
0.8824	High Similarity	NPC123722
0.8824	High Similarity	NPC276466
0.8824	High Similarity	NPC123228
0.8824	High Similarity	NPC151167
0.8824	High Similarity	NPC286683
0.8824	High Similarity	NPC16651
0.8824	High Similarity	NPC5018
0.8824	High Similarity	NPC32163
0.8786	High Similarity	NPC176814
0.8786	High Similarity	NPC4982
0.8786	High Similarity	NPC5310
0.8786	High Similarity	NPC68779
0.8786	High Similarity	NPC300776
0.8784	High Similarity	NPC37220
0.8768	High Similarity	NPC477694
0.8768	High Similarity	NPC477705
0.8766	High Similarity	NPC76687
0.8759	High Similarity	NPC50954
0.875	High Similarity	NPC179777
0.875	High Similarity	NPC274356
0.875	High Similarity	NPC84076
0.875	High Similarity	NPC303680
0.875	High Similarity	NPC90128
0.8725	High Similarity	NPC234152
0.8723	High Similarity	NPC204592
0.8716	High Similarity	NPC474903
0.8714	High Similarity	NPC327410
0.8707	High Similarity	NPC153620
0.8707	High Similarity	NPC24257
0.8705	High Similarity	NPC477706
0.8699	High Similarity	NPC207732
0.8676	High Similarity	NPC53305
0.8676	High Similarity	NPC257589
0.8675	High Similarity	NPC25127
0.8671	High Similarity	NPC284409
0.8667	High Similarity	NPC267091
0.8654	High Similarity	NPC475738
0.8643	High Similarity	NPC50763
0.8643	High Similarity	NPC239302
0.8639	High Similarity	NPC30890
0.8639	High Similarity	NPC472560
0.8627	High Similarity	NPC226759
0.8613	High Similarity	NPC92207
0.8613	High Similarity	NPC127937
0.8609	High Similarity	NPC131121
0.86	High Similarity	NPC243891
0.8592	High Similarity	NPC95485
0.8592	High Similarity	NPC89504
0.8592	High Similarity	NPC88065
0.859	High Similarity	NPC100420
0.859	High Similarity	NPC100425
0.8581	High Similarity	NPC88345
0.8581	High Similarity	NPC295009
0.8581	High Similarity	NPC260640
0.8562	High Similarity	NPC471405
0.8562	High Similarity	NPC312256
0.8553	High Similarity	NPC287504
0.8552	High Similarity	NPC326065
0.8551	High Similarity	NPC64948
0.8543	High Similarity	NPC151425
0.8533	High Similarity	NPC261322
0.8533	High Similarity	NPC237441
0.8533	High Similarity	NPC205054
0.8529	High Similarity	NPC242372
0.8529	High Similarity	NPC4181
0.8529	High Similarity	NPC164778
0.8529	High Similarity	NPC249788
0.8529	High Similarity	NPC474691
0.8529	High Similarity	NPC257976
0.8521	High Similarity	NPC45404
0.8521	High Similarity	NPC144662
0.8516	High Similarity	NPC239818
0.8516	High Similarity	NPC218471
0.8516	High Similarity	NPC285973
0.8516	High Similarity	NPC225624
0.8514	High Similarity	NPC157133
0.8514	High Similarity	NPC160777
0.8514	High Similarity	NPC73416
0.8511	High Similarity	NPC111888
0.85	High Similarity	NPC275950
0.85	High Similarity	NPC172673
0.8497	Intermediate Similarity	NPC10205
0.8497	Intermediate Similarity	NPC300757
0.8497	Intermediate Similarity	NPC180901
0.8493	Intermediate Similarity	NPC110419
0.8489	Intermediate Similarity	NPC226661
0.8487	Intermediate Similarity	NPC308555
0.8487	Intermediate Similarity	NPC35544
0.8487	Intermediate Similarity	NPC104728
0.8483	Intermediate Similarity	NPC474784
0.8478	Intermediate Similarity	NPC276014
0.8477	Intermediate Similarity	NPC472279
0.8477	Intermediate Similarity	NPC32079
0.8477	Intermediate Similarity	NPC477700
0.8467	Intermediate Similarity	NPC55327
0.8467	Intermediate Similarity	NPC273686
0.8467	Intermediate Similarity	NPC216223
0.8467	Intermediate Similarity	NPC312404
0.8467	Intermediate Similarity	NPC145569
0.8462	Intermediate Similarity	NPC139519
0.8462	Intermediate Similarity	NPC113295
0.8456	Intermediate Similarity	NPC165389
0.8456	Intermediate Similarity	NPC114298
0.8452	Intermediate Similarity	NPC215375
0.8452	Intermediate Similarity	NPC62518
0.8452	Intermediate Similarity	NPC68619
0.8451	Intermediate Similarity	NPC283823
0.8451	Intermediate Similarity	NPC159418
0.8451	Intermediate Similarity	NPC205915
0.8446	Intermediate Similarity	NPC229787
0.8446	Intermediate Similarity	NPC309169
0.8446	Intermediate Similarity	NPC196941
0.8446	Intermediate Similarity	NPC142165
0.8446	Intermediate Similarity	NPC275278
0.8446	Intermediate Similarity	NPC105213
0.8442	Intermediate Similarity	NPC109765
0.844	Intermediate Similarity	NPC476345
0.8431	Intermediate Similarity	NPC194095
0.8431	Intermediate Similarity	NPC327032
0.8431	Intermediate Similarity	NPC191046
0.8425	Intermediate Similarity	NPC100675
0.8425	Intermediate Similarity	NPC78987
0.8425	Intermediate Similarity	NPC29599
0.8425	Intermediate Similarity	NPC82336
0.8421	Intermediate Similarity	NPC220577
0.8421	Intermediate Similarity	NPC272566
0.8421	Intermediate Similarity	NPC144283
0.8417	Intermediate Similarity	NPC117237
0.8417	Intermediate Similarity	NPC203719
0.8408	Intermediate Similarity	NPC469512
0.8403	Intermediate Similarity	NPC230968
0.8403	Intermediate Similarity	NPC324929
0.8403	Intermediate Similarity	NPC102260
0.84	Intermediate Similarity	NPC472969
0.84	Intermediate Similarity	NPC52692
0.8397	Intermediate Similarity	NPC472961
0.8397	Intermediate Similarity	NPC472962
0.8394	Intermediate Similarity	NPC18984
0.8394	Intermediate Similarity	NPC229084
0.8394	Intermediate Similarity	NPC163083
0.8394	Intermediate Similarity	NPC106659
0.8394	Intermediate Similarity	NPC160900
0.8389	Intermediate Similarity	NPC225351
0.8389	Intermediate Similarity	NPC296575
0.8389	Intermediate Similarity	NPC287495
0.8389	Intermediate Similarity	NPC9370
0.8389	Intermediate Similarity	NPC224687
0.8387	Intermediate Similarity	NPC472860
0.8387	Intermediate Similarity	NPC167595
0.8387	Intermediate Similarity	NPC202495
0.8385	Intermediate Similarity	NPC178737
0.8385	Intermediate Similarity	NPC469506
0.8382	Intermediate Similarity	NPC201777
0.838	Intermediate Similarity	NPC227002
0.838	Intermediate Similarity	NPC471505
0.838	Intermediate Similarity	NPC106739
0.8378	Intermediate Similarity	NPC469615
0.8378	Intermediate Similarity	NPC254659
0.8378	Intermediate Similarity	NPC473090
0.8377	Intermediate Similarity	NPC268008
0.8377	Intermediate Similarity	NPC254163
0.8369	Intermediate Similarity	NPC181079
0.8369	Intermediate Similarity	NPC244246
0.8369	Intermediate Similarity	NPC215941
0.8369	Intermediate Similarity	NPC319282
0.8369	Intermediate Similarity	NPC275724
0.8369	Intermediate Similarity	NPC137427
0.8369	Intermediate Similarity	NPC65935
0.8369	Intermediate Similarity	NPC123196
0.8369	Intermediate Similarity	NPC311419
0.8369	Intermediate Similarity	NPC173308
0.8367	Intermediate Similarity	NPC253481
0.8367	Intermediate Similarity	NPC31751
0.8367	Intermediate Similarity	NPC104956
0.8367	Intermediate Similarity	NPC84273
0.8367	Intermediate Similarity	NPC472410
0.8367	Intermediate Similarity	NPC253722
0.8366	Intermediate Similarity	NPC157898
0.8366	Intermediate Similarity	NPC137813
0.8366	Intermediate Similarity	NPC164912
0.8366	Intermediate Similarity	NPC44730

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 NPC46880 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	892
0.2-0.3	1451
0.3-0.4	2565
0.4-0.5	2065
0.5-0.6	1155
0.6-0.7	585
0.7-0.8	132
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD6143	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD9494	Approved
0.84	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8205	Intermediate Similarity	NPD3882	Suspended
0.8052	Intermediate Similarity	NPD7458	Discontinued
0.8	Intermediate Similarity	NPD7028	Phase 2
0.8	Intermediate Similarity	NPD7685	Pre-registration
0.7962	Intermediate Similarity	NPD2801	Approved
0.7917	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1934	Approved
0.7883	Intermediate Similarity	NPD5536	Phase 2
0.7881	Intermediate Similarity	NPD4628	Phase 3
0.7879	Intermediate Similarity	NPD7074	Phase 3
0.7875	Intermediate Similarity	NPD6234	Discontinued
0.7832	Intermediate Similarity	NPD2798	Approved
0.7818	Intermediate Similarity	NPD7054	Approved
0.7801	Intermediate Similarity	NPD3972	Approved
0.78	Intermediate Similarity	NPD2344	Approved
0.7785	Intermediate Similarity	NPD37	Approved
0.7771	Intermediate Similarity	NPD7472	Approved
0.775	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2935	Discontinued
0.7721	Intermediate Similarity	NPD5283	Phase 1
0.7697	Intermediate Similarity	NPD7473	Discontinued
0.7692	Intermediate Similarity	NPD1876	Approved
0.7669	Intermediate Similarity	NPD7199	Phase 2
0.7667	Intermediate Similarity	NPD2799	Discontinued
0.764	Intermediate Similarity	NPD4965	Approved
0.764	Intermediate Similarity	NPD4967	Phase 2
0.764	Intermediate Similarity	NPD4966	Approved
0.7635	Intermediate Similarity	NPD943	Approved
0.7633	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6232	Discontinued
0.7619	Intermediate Similarity	NPD6797	Phase 2
0.7613	Intermediate Similarity	NPD1511	Approved
0.7607	Intermediate Similarity	NPD5494	Approved
0.7597	Intermediate Similarity	NPD2309	Approved
0.7593	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD230	Phase 1
0.7578	Intermediate Similarity	NPD5978	Approved
0.7578	Intermediate Similarity	NPD5977	Approved
0.7576	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD228	Approved
0.7574	Intermediate Similarity	NPD7251	Discontinued
0.7572	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7228	Approved
0.7532	Intermediate Similarity	NPD8166	Discontinued
0.7532	Intermediate Similarity	NPD4110	Phase 3
0.7532	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6166	Phase 2
0.7529	Intermediate Similarity	NPD7808	Phase 3
0.7518	Intermediate Similarity	NPD1357	Approved
0.7517	Intermediate Similarity	NPD1240	Approved
0.7516	Intermediate Similarity	NPD1512	Approved
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD3764	Approved
0.7469	Intermediate Similarity	NPD3817	Phase 2
0.7468	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1933	Approved
0.7467	Intermediate Similarity	NPD6355	Discontinued
0.7467	Intermediate Similarity	NPD447	Suspended
0.7448	Intermediate Similarity	NPD1283	Approved
0.7434	Intermediate Similarity	NPD1510	Phase 2
0.7432	Intermediate Similarity	NPD3027	Phase 3
0.7431	Intermediate Similarity	NPD1608	Approved
0.7426	Intermediate Similarity	NPD3022	Approved
0.7426	Intermediate Similarity	NPD3021	Approved
0.7417	Intermediate Similarity	NPD1607	Approved
0.7391	Intermediate Similarity	NPD6386	Approved
0.7391	Intermediate Similarity	NPD6873	Phase 2
0.7391	Intermediate Similarity	NPD6385	Approved
0.7375	Intermediate Similarity	NPD824	Approved
0.7375	Intermediate Similarity	NPD3455	Phase 2
0.7372	Intermediate Similarity	NPD6190	Approved
0.7372	Intermediate Similarity	NPD2354	Approved
0.7368	Intermediate Similarity	NPD6559	Discontinued
0.7365	Intermediate Similarity	NPD3926	Phase 2
0.7361	Intermediate Similarity	NPD3705	Approved
0.7338	Intermediate Similarity	NPD7266	Discontinued
0.7338	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4380	Phase 2
0.731	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7003	Approved
0.7296	Intermediate Similarity	NPD6273	Approved
0.7294	Intermediate Similarity	NPD5844	Phase 1
0.729	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3620	Phase 2
0.7285	Intermediate Similarity	NPD4060	Phase 1
0.7278	Intermediate Similarity	NPD6799	Approved
0.7273	Intermediate Similarity	NPD7075	Discontinued
0.7273	Intermediate Similarity	NPD1651	Approved
0.7267	Intermediate Similarity	NPD3268	Approved
0.7241	Intermediate Similarity	NPD1281	Approved
0.7241	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2346	Discontinued
0.7222	Intermediate Similarity	NPD17	Approved
0.7222	Intermediate Similarity	NPD6599	Discontinued
0.7203	Intermediate Similarity	NPD9545	Approved
0.72	Intermediate Similarity	NPD7095	Approved
0.72	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3750	Approved
0.7195	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7819	Suspended
0.7193	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD9269	Phase 2
0.7179	Intermediate Similarity	NPD1549	Phase 2
0.7162	Intermediate Similarity	NPD2797	Approved
0.716	Intermediate Similarity	NPD5242	Approved
0.7152	Intermediate Similarity	NPD2313	Discontinued
0.7152	Intermediate Similarity	NPD3887	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7126	Intermediate Similarity	NPD919	Approved
0.7125	Intermediate Similarity	NPD2532	Approved
0.7125	Intermediate Similarity	NPD2534	Approved
0.7125	Intermediate Similarity	NPD2533	Approved
0.7115	Intermediate Similarity	NPD1471	Phase 3
0.7115	Intermediate Similarity	NPD2353	Approved
0.7115	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1241	Discontinued
0.7091	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD8313	Approved
0.7069	Intermediate Similarity	NPD7240	Approved
0.7066	Intermediate Similarity	NPD3749	Approved
0.7063	Intermediate Similarity	NPD4357	Discontinued
0.7059	Intermediate Similarity	NPD2979	Phase 3
0.7055	Intermediate Similarity	NPD3847	Discontinued
0.7055	Intermediate Similarity	NPD3226	Approved
0.7051	Intermediate Similarity	NPD2796	Approved
0.7051	Intermediate Similarity	NPD2438	Suspended
0.7048	Intermediate Similarity	NPD2296	Approved
0.7048	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1203	Approved
0.7041	Intermediate Similarity	NPD2821	Approved
0.7041	Intermediate Similarity	NPD1247	Approved
0.7041	Intermediate Similarity	NPD8127	Discontinued
0.703	Intermediate Similarity	NPD6801	Discontinued
0.7027	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5647	Approved
0.6994	Remote Similarity	NPD1653	Approved
0.6993	Remote Similarity	NPD4062	Phase 3
0.6993	Remote Similarity	NPD6233	Phase 2
0.6988	Remote Similarity	NPD2977	Approved
0.6988	Remote Similarity	NPD2978	Approved
0.6987	Remote Similarity	NPD4308	Phase 3
0.6986	Remote Similarity	NPD2932	Approved
0.6986	Remote Similarity	NPD4626	Approved
0.6986	Remote Similarity	NPD3019	Approved
0.6975	Remote Similarity	NPD5049	Phase 3
0.697	Remote Similarity	NPD7411	Suspended
0.6968	Remote Similarity	NPD2492	Phase 1
0.6966	Remote Similarity	NPD8434	Phase 2
0.6962	Remote Similarity	NPD5958	Discontinued
0.6959	Remote Similarity	NPD1481	Phase 2
0.6951	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5353	Approved
0.6936	Remote Similarity	NPD3751	Discontinued
0.6933	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3266	Approved
0.6933	Remote Similarity	NPD1470	Approved
0.6933	Remote Similarity	NPD3267	Approved
0.6928	Remote Similarity	NPD7577	Discontinued
0.6928	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2800	Approved
0.6918	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD9268	Approved
0.6914	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6876	Approved
0.6909	Remote Similarity	NPD6875	Approved
0.6908	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6832	Phase 2
0.6893	Remote Similarity	NPD7280	Phase 3
0.6893	Remote Similarity	NPD7281	Phase 3
0.6892	Remote Similarity	NPD1535	Discovery
0.6892	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD8032	Phase 2
0.6879	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3748	Approved
0.6867	Remote Similarity	NPD7110	Phase 1
0.6867	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6653	Approved
0.6855	Remote Similarity	NPD4534	Discontinued
0.6849	Remote Similarity	NPD1894	Discontinued
0.6848	Remote Similarity	NPD2649	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