NPASS Compound

Structure

CID4286 OpenBabel06191715322D 22 24 0 0 1 0 0 0 0 0999 V2000 0.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7934 -0.6088 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 -6.0622 0.5000 0.0000 C 0 0 0 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 -0.8660 1.5000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 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 -4.3301 1.5000 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 -4.3301 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 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 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 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 4 22 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 14 19 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 6 0 0 0 17 18 1 0 0 0 0 17 21 1 1 0 0 0 19 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.19
Volume:	327.336
LogP:	2.966
LogD:	2.818
LogS:	-3.929
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.881
Synthetic Accessibility Score:	3.913
Fsp3:	0.579
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:	-4.665
MDCK Permeability:	2.280125772813335e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.735
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.357
30% Bioavailability (F30%):	0.051

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.949
Plasma Protein Binding (PPB):	82.9316177368164%
Volume Distribution (VD):	1.352
Pgp-substrate:	19.62506866455078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.393
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.847
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.401
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.115
CYP3A4-substrate:	0.539

ADMET: Excretion

Clearance (CL):	9.82
Half-life (T1/2):	0.643

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.227
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.873
Carcinogencity:	0.587
Eye Corrosion:	0.004
Eye Irritation:	0.096
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC4286

Natural Product ID:	NPC4286
*Common Name:**	3Beta-Hydroxy-13-Hydroxymethyl-12-Methoxy-Ent-Podocarp-6,8,11,13-Tetraene
IUPAC Name:	(2S,4aR,10aS)-7-(hydroxymethyl)-6-methoxy-1,1,4a-trimethyl-2,3,4,10a-tetrahydrophenanthren-2-ol
Synonyms:
Standard InCHIKey:	OQWQQASPTCXQLO-AOIWGVFYSA-N
Standard InCHI:	InChI=1S/C19H26O3/c1-18(2)16-6-5-12-9-13(11-20)15(22-4)10-14(12)19(16,3)8-7-17(18)21/h5-6,9-10,16-17,20-21H,7-8,11H2,1-4H3/t16-,17+,19+/m1/s1
SMILES:	CC1(C)[C@H]2C=Cc3cc(CO)c(cc3[C@]2(C)CC[C@@H]1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3103101
PubChem CID:	76317305
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO670	Hyrtios gumminae	Species	Thorectidae	Eukaryota	n.a.	Thai	n.a.	PMID[19788270]
NPO8960	Flueggea virosa	Species	Phyllanthaceae	Eukaryota	roots	Pingtung County, Taiwan	2011-SEP	PMID[24400834]
NPO1253	Nasturtium officinale	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1253	Nasturtium officinale	Species	Brassicaceae	Eukaryota	Herb	n.a.	n.a.	Database[FooDB]
NPO1253	Nasturtium officinale	Species	Brassicaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO1253	Nasturtium officinale	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO1253	Nasturtium officinale	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1253	Nasturtium officinale	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO1253	Nasturtium officinale	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1253	Nasturtium officinale	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1253	Nasturtium officinale	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8960	Flueggea virosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO670	Hyrtios gumminae	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
IC50	1
Others	1

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Ratio IC50/EC50	=	4.9	n.a.	PMID[489554]
NPT27	Others	Unspecified		IC50	=	150900.0	nM	PMID[489554]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	EC50	=	30500.0	nM	PMID[489554]

☑ 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 NPC4286 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	347
0.1-0.2	1498
0.2-0.3	3055
0.3-0.4	9061
0.4-0.5	9936
0.5-0.6	5711
0.6-0.7	9816
0.7-0.8	3002
0.8-0.85	216
0.85-0.9	47
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC76119
0.9746	High Similarity	NPC152946
0.9153	High Similarity	NPC312105
0.9076	High Similarity	NPC477136
0.904	High Similarity	NPC186889
0.888	High Similarity	NPC470726
0.8852	High Similarity	NPC260832
0.8852	High Similarity	NPC135467
0.8833	High Similarity	NPC38893
0.8833	High Similarity	NPC219112
0.8833	High Similarity	NPC477137
0.8833	High Similarity	NPC308311
0.8828	High Similarity	NPC196193
0.881	High Similarity	NPC470724
0.878	High Similarity	NPC129176
0.875	High Similarity	NPC192948
0.875	High Similarity	NPC35797
0.875	High Similarity	NPC147179
0.873	High Similarity	NPC105031
0.8729	High Similarity	NPC470723
0.8699	High Similarity	NPC103916
0.8692	High Similarity	NPC85595
0.8689	High Similarity	NPC63010
0.8689	High Similarity	NPC471671
0.8689	High Similarity	NPC154030
0.8682	High Similarity	NPC470727
0.8682	High Similarity	NPC249425
0.8678	High Similarity	NPC469663
0.8678	High Similarity	NPC308828
0.8678	High Similarity	NPC92
0.8672	High Similarity	NPC223912
0.8667	High Similarity	NPC470837
0.8667	High Similarity	NPC268160
0.8655	High Similarity	NPC250323
0.8651	High Similarity	NPC75432
0.8626	High Similarity	NPC227719
0.8618	High Similarity	NPC469644
0.8607	High Similarity	NPC304510
0.8607	High Similarity	NPC25648
0.8607	High Similarity	NPC172219
0.8594	High Similarity	NPC471077
0.8583	High Similarity	NPC124030
0.8583	High Similarity	NPC293801
0.8537	High Similarity	NPC469609
0.8527	High Similarity	NPC215300
0.8527	High Similarity	NPC201069
0.8516	High Similarity	NPC170485
0.85	High Similarity	NPC228425
0.8492	Intermediate Similarity	NPC30462
0.8492	Intermediate Similarity	NPC188997
0.8487	Intermediate Similarity	NPC13482
0.848	Intermediate Similarity	NPC100108
0.848	Intermediate Similarity	NPC277798
0.8468	Intermediate Similarity	NPC151197
0.845	Intermediate Similarity	NPC53781
0.8433	Intermediate Similarity	NPC68292
0.843	Intermediate Similarity	NPC35344
0.843	Intermediate Similarity	NPC141003
0.8425	Intermediate Similarity	NPC261992
0.8421	Intermediate Similarity	NPC473107
0.8417	Intermediate Similarity	NPC260323
0.8417	Intermediate Similarity	NPC176279
0.8409	Intermediate Similarity	NPC289624
0.8409	Intermediate Similarity	NPC27578
0.8385	Intermediate Similarity	NPC38017
0.8374	Intermediate Similarity	NPC33900
0.8374	Intermediate Similarity	NPC471668
0.8361	Intermediate Similarity	NPC195922
0.8359	Intermediate Similarity	NPC138248
0.8359	Intermediate Similarity	NPC228503
0.8347	Intermediate Similarity	NPC228452
0.8346	Intermediate Similarity	NPC57199
0.8333	Intermediate Similarity	NPC141782
0.8333	Intermediate Similarity	NPC282508
0.8333	Intermediate Similarity	NPC153019
0.8333	Intermediate Similarity	NPC102639
0.8333	Intermediate Similarity	NPC132720
0.8321	Intermediate Similarity	NPC206028
0.8321	Intermediate Similarity	NPC472795
0.8321	Intermediate Similarity	NPC472797
0.8321	Intermediate Similarity	NPC472796
0.8308	Intermediate Similarity	NPC473221
0.8295	Intermediate Similarity	NPC278955
0.8295	Intermediate Similarity	NPC105718
0.8295	Intermediate Similarity	NPC81641
0.8295	Intermediate Similarity	NPC113495
0.8295	Intermediate Similarity	NPC9067
0.8293	Intermediate Similarity	NPC283169
0.8286	Intermediate Similarity	NPC471608
0.8273	Intermediate Similarity	NPC473845
0.8271	Intermediate Similarity	NPC321502
0.8271	Intermediate Similarity	NPC472798
0.8271	Intermediate Similarity	NPC165612
0.8268	Intermediate Similarity	NPC476633
0.8258	Intermediate Similarity	NPC254000
0.825	Intermediate Similarity	NPC474272
0.8244	Intermediate Similarity	NPC23012
0.8244	Intermediate Similarity	NPC307050
0.8244	Intermediate Similarity	NPC277458
0.8244	Intermediate Similarity	NPC38604
0.8244	Intermediate Similarity	NPC211179
0.824	Intermediate Similarity	NPC329980
0.824	Intermediate Similarity	NPC164649
0.824	Intermediate Similarity	NPC190514
0.824	Intermediate Similarity	NPC48342
0.8235	Intermediate Similarity	NPC472980
0.8235	Intermediate Similarity	NPC151477
0.8231	Intermediate Similarity	NPC82299
0.8226	Intermediate Similarity	NPC474387
0.8226	Intermediate Similarity	NPC154511
0.8226	Intermediate Similarity	NPC247858
0.8226	Intermediate Similarity	NPC137496
0.8226	Intermediate Similarity	NPC474358
0.8226	Intermediate Similarity	NPC257540
0.8222	Intermediate Similarity	NPC37410
0.8217	Intermediate Similarity	NPC181334
0.8217	Intermediate Similarity	NPC248557
0.8217	Intermediate Similarity	NPC61685
0.8209	Intermediate Similarity	NPC211352
0.8209	Intermediate Similarity	NPC469610
0.8203	Intermediate Similarity	NPC77789
0.8203	Intermediate Similarity	NPC18128
0.8203	Intermediate Similarity	NPC150026
0.8203	Intermediate Similarity	NPC471794
0.8203	Intermediate Similarity	NPC478058
0.8197	Intermediate Similarity	NPC46940
0.8197	Intermediate Similarity	NPC98372
0.8197	Intermediate Similarity	NPC302371
0.8195	Intermediate Similarity	NPC8899
0.8195	Intermediate Similarity	NPC312341
0.8195	Intermediate Similarity	NPC160623
0.8189	Intermediate Similarity	NPC32322
0.8189	Intermediate Similarity	NPC259703
0.8189	Intermediate Similarity	NPC328504
0.8188	Intermediate Similarity	NPC265075
0.8182	Intermediate Similarity	NPC471518
0.8182	Intermediate Similarity	NPC16577
0.8182	Intermediate Similarity	NPC471519
0.8175	Intermediate Similarity	NPC184613
0.8175	Intermediate Similarity	NPC93071
0.8175	Intermediate Similarity	NPC184302
0.8169	Intermediate Similarity	NPC212142
0.8168	Intermediate Similarity	NPC469386
0.8167	Intermediate Similarity	NPC201959
0.8167	Intermediate Similarity	NPC75440
0.8162	Intermediate Similarity	NPC472800
0.8162	Intermediate Similarity	NPC472648
0.8162	Intermediate Similarity	NPC170328
0.8162	Intermediate Similarity	NPC471670
0.8162	Intermediate Similarity	NPC191462
0.8162	Intermediate Similarity	NPC133463
0.8162	Intermediate Similarity	NPC472647
0.8162	Intermediate Similarity	NPC472649
0.8162	Intermediate Similarity	NPC206525
0.8154	Intermediate Similarity	NPC266705
0.8154	Intermediate Similarity	NPC228771
0.8154	Intermediate Similarity	NPC29008
0.8151	Intermediate Similarity	NPC21594
0.8148	Intermediate Similarity	NPC311256
0.8148	Intermediate Similarity	NPC209199
0.8148	Intermediate Similarity	NPC27394
0.8148	Intermediate Similarity	NPC213122
0.8145	Intermediate Similarity	NPC474486
0.814	Intermediate Similarity	NPC471187
0.8134	Intermediate Similarity	NPC321086
0.8134	Intermediate Similarity	NPC469611
0.8134	Intermediate Similarity	NPC59239
0.813	Intermediate Similarity	NPC715
0.8129	Intermediate Similarity	NPC20631
0.8129	Intermediate Similarity	NPC93640
0.8125	Intermediate Similarity	NPC48623
0.8125	Intermediate Similarity	NPC474115
0.8125	Intermediate Similarity	NPC168707
0.812	Intermediate Similarity	NPC470725
0.812	Intermediate Similarity	NPC99795
0.8115	Intermediate Similarity	NPC275627
0.8115	Intermediate Similarity	NPC470770
0.8115	Intermediate Similarity	NPC266937
0.8115	Intermediate Similarity	NPC95716
0.811	Intermediate Similarity	NPC282255
0.811	Intermediate Similarity	NPC3239
0.8106	Intermediate Similarity	NPC53986
0.8106	Intermediate Similarity	NPC38664
0.8106	Intermediate Similarity	NPC47288
0.8106	Intermediate Similarity	NPC274717
0.8102	Intermediate Similarity	NPC242715
0.8102	Intermediate Similarity	NPC266006
0.8102	Intermediate Similarity	NPC71465
0.8102	Intermediate Similarity	NPC472646
0.8102	Intermediate Similarity	NPC56329
0.8099	Intermediate Similarity	NPC58865
0.8095	Intermediate Similarity	NPC283616
0.8095	Intermediate Similarity	NPC474214
0.8095	Intermediate Similarity	NPC474040
0.8095	Intermediate Similarity	NPC131118
0.8092	Intermediate Similarity	NPC325294
0.8092	Intermediate Similarity	NPC276212
0.8092	Intermediate Similarity	NPC321822
0.8088	Intermediate Similarity	NPC258780
0.8088	Intermediate Similarity	NPC313081

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 NPC4286 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	944
0.2-0.3	1364
0.3-0.4	2625
0.4-0.5	1969
0.5-0.6	1121
0.6-0.7	655
0.7-0.8	148
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8702	High Similarity	NPD4097	Suspended
0.8661	High Similarity	NPD6917	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD4626	Approved
0.8397	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8281	Intermediate Similarity	NPD5327	Phase 3
0.8271	Intermediate Similarity	NPD3620	Phase 2
0.8271	Intermediate Similarity	NPD4140	Approved
0.8271	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.824	Intermediate Similarity	NPD3091	Approved
0.8231	Intermediate Similarity	NPD4624	Approved
0.8209	Intermediate Similarity	NPD5735	Approved
0.8182	Intermediate Similarity	NPD4625	Phase 3
0.8175	Intermediate Similarity	NPD5691	Approved
0.8058	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD6353	Approved
0.8	Intermediate Similarity	NPD4749	Approved
0.8	Intermediate Similarity	NPD4060	Phase 1
0.7985	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD3092	Approved
0.7969	Intermediate Similarity	NPD3095	Discontinued
0.7939	Intermediate Similarity	NPD1283	Approved
0.7895	Intermediate Similarity	NPD2861	Phase 2
0.7891	Intermediate Similarity	NPD1651	Approved
0.7879	Intermediate Similarity	NPD3094	Phase 2
0.7846	Intermediate Similarity	NPD1610	Phase 2
0.7836	Intermediate Similarity	NPD4908	Phase 1
0.7803	Intermediate Similarity	NPD8651	Approved
0.7803	Intermediate Similarity	NPD6696	Suspended
0.776	Intermediate Similarity	NPD7635	Approved
0.7746	Intermediate Similarity	NPD7003	Approved
0.7737	Intermediate Similarity	NPD2238	Phase 2
0.7717	Intermediate Similarity	NPD7157	Approved
0.771	Intermediate Similarity	NPD1281	Approved
0.7708	Intermediate Similarity	NPD7041	Phase 2
0.7708	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD5283	Phase 1
0.7692	Intermediate Similarity	NPD2932	Approved
0.7676	Intermediate Similarity	NPD6674	Discontinued
0.7661	Intermediate Similarity	NPD4750	Phase 3
0.7656	Intermediate Similarity	NPD7340	Approved
0.7652	Intermediate Similarity	NPD2232	Approved
0.7652	Intermediate Similarity	NPD2233	Approved
0.7652	Intermediate Similarity	NPD2230	Approved
0.7647	Intermediate Similarity	NPD3027	Phase 3
0.7642	Intermediate Similarity	NPD2342	Discontinued
0.763	Intermediate Similarity	NPD5736	Approved
0.7594	Intermediate Similarity	NPD1669	Approved
0.7589	Intermediate Similarity	NPD6100	Approved
0.7589	Intermediate Similarity	NPD6099	Approved
0.7581	Intermediate Similarity	NPD2684	Approved
0.7578	Intermediate Similarity	NPD6671	Approved
0.7568	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD1398	Phase 1
0.7557	Intermediate Similarity	NPD4059	Approved
0.7557	Intermediate Similarity	NPD3019	Approved
0.7554	Intermediate Similarity	NPD3657	Discovery
0.7538	Intermediate Similarity	NPD1548	Phase 1
0.7535	Intermediate Similarity	NPD5763	Approved
0.7535	Intermediate Similarity	NPD5762	Approved
0.7534	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4108	Discontinued
0.75	Intermediate Similarity	NPD2157	Approved
0.75	Intermediate Similarity	NPD290	Approved
0.75	Intermediate Similarity	NPD3020	Approved
0.7483	Intermediate Similarity	NPD6273	Approved
0.7482	Intermediate Similarity	NPD1613	Approved
0.7482	Intermediate Similarity	NPD2979	Phase 3
0.7482	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1357	Approved
0.7479	Intermediate Similarity	NPD288	Approved
0.7465	Intermediate Similarity	NPD2438	Suspended
0.7464	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1611	Approved
0.7442	Intermediate Similarity	NPD709	Approved
0.7432	Intermediate Similarity	NPD5699	Approved
0.7426	Intermediate Similarity	NPD3691	Phase 2
0.7426	Intermediate Similarity	NPD6584	Phase 3
0.7426	Intermediate Similarity	NPD3690	Phase 2
0.7424	Intermediate Similarity	NPD2667	Approved
0.7424	Intermediate Similarity	NPD2668	Approved
0.7424	Intermediate Similarity	NPD1778	Approved
0.741	Intermediate Similarity	NPD8032	Phase 2
0.741	Intermediate Similarity	NPD6663	Approved
0.7402	Intermediate Similarity	NPD228	Approved
0.7395	Intermediate Similarity	NPD1809	Phase 2
0.7395	Intermediate Similarity	NPD844	Approved
0.7388	Intermediate Similarity	NPD2231	Phase 2
0.7388	Intermediate Similarity	NPD2235	Phase 2
0.7381	Intermediate Similarity	NPD5451	Approved
0.7379	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD7037	Approved
0.7357	Intermediate Similarity	NPD3110	Approved
0.7357	Intermediate Similarity	NPD3109	Approved
0.7353	Intermediate Similarity	NPD2797	Approved
0.7344	Intermediate Similarity	NPD7843	Approved
0.7343	Intermediate Similarity	NPD2935	Discontinued
0.7338	Intermediate Similarity	NPD7294	Phase 1
0.7317	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5177	Phase 3
0.7305	Intermediate Similarity	NPD5124	Phase 1
0.7305	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD37	Approved
0.7295	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7741	Discontinued
0.7266	Intermediate Similarity	NPD7095	Approved
0.725	Intermediate Similarity	NPD2859	Approved
0.725	Intermediate Similarity	NPD2860	Approved
0.7246	Intermediate Similarity	NPD1712	Approved
0.7244	Intermediate Similarity	NPD3021	Approved
0.7244	Intermediate Similarity	NPD3022	Approved
0.7239	Intermediate Similarity	NPD3496	Discontinued
0.7227	Intermediate Similarity	NPD845	Approved
0.7222	Intermediate Similarity	NPD2531	Phase 2
0.7222	Intermediate Similarity	NPD4477	Approved
0.7222	Intermediate Similarity	NPD4476	Approved
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7218	Intermediate Similarity	NPD3443	Approved
0.7218	Intermediate Similarity	NPD3444	Approved
0.7218	Intermediate Similarity	NPD5585	Approved
0.7218	Intermediate Similarity	NPD3445	Approved
0.7215	Intermediate Similarity	NPD2969	Approved
0.7215	Intermediate Similarity	NPD2970	Approved
0.7209	Intermediate Similarity	NPD1138	Approved
0.7206	Intermediate Similarity	NPD6582	Phase 2
0.7206	Intermediate Similarity	NPD6583	Phase 3
0.7203	Intermediate Similarity	NPD4538	Approved
0.7203	Intermediate Similarity	NPD4536	Approved
0.7203	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD600	Approved
0.7194	Intermediate Similarity	NPD596	Approved
0.7194	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6355	Discontinued
0.7176	Intermediate Similarity	NPD6387	Discontinued
0.717	Intermediate Similarity	NPD2489	Approved
0.717	Intermediate Similarity	NPD27	Approved
0.7167	Intermediate Similarity	NPD2934	Approved
0.7167	Intermediate Similarity	NPD2933	Approved
0.7164	Intermediate Similarity	NPD5846	Approved
0.7164	Intermediate Similarity	NPD6516	Phase 2
0.7164	Intermediate Similarity	NPD2286	Discontinued
0.7164	Intermediate Similarity	NPD1751	Approved
0.7161	Intermediate Similarity	NPD4967	Phase 2
0.7161	Intermediate Similarity	NPD4965	Approved
0.7161	Intermediate Similarity	NPD4966	Approved
0.7154	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7743	Approved
0.7153	Intermediate Similarity	NPD7742	Approved
0.7143	Intermediate Similarity	NPD5929	Approved
0.7143	Intermediate Similarity	NPD6331	Phase 2
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD968	Approved
0.7143	Intermediate Similarity	NPD3892	Phase 2
0.7133	Intermediate Similarity	NPD6090	Discontinued
0.7132	Intermediate Similarity	NPD1137	Approved
0.7132	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1139	Approved
0.7132	Intermediate Similarity	NPD3972	Approved
0.7123	Intermediate Similarity	NPD2424	Discontinued
0.7122	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3023	Approved
0.7111	Intermediate Similarity	NPD3026	Approved
0.7097	Intermediate Similarity	NPD2560	Approved
0.7097	Intermediate Similarity	NPD2563	Approved
0.7097	Intermediate Similarity	NPD846	Approved
0.7097	Intermediate Similarity	NPD940	Approved
0.7095	Intermediate Similarity	NPD5241	Discontinued
0.7092	Intermediate Similarity	NPD3268	Approved
0.7092	Intermediate Similarity	NPD6798	Discontinued
0.7092	Intermediate Similarity	NPD1039	Discontinued
0.709	Intermediate Similarity	NPD3025	Approved
0.709	Intermediate Similarity	NPD3024	Approved
0.709	Intermediate Similarity	NPD4093	Discontinued
0.708	Intermediate Similarity	NPD3685	Discontinued
0.7077	Intermediate Similarity	NPD821	Approved
0.7077	Intermediate Similarity	NPD5535	Approved
0.707	Intermediate Similarity	NPD5709	Phase 3
0.7068	Intermediate Similarity	NPD7644	Approved
0.7067	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1091	Approved
0.7055	Intermediate Similarity	NPD2346	Discontinued
0.7051	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6666	Approved
0.7047	Intermediate Similarity	NPD6667	Approved
0.7044	Intermediate Similarity	NPD3051	Approved
0.7042	Intermediate Similarity	NPD840	Approved
0.7042	Intermediate Similarity	NPD839	Approved
0.7037	Intermediate Similarity	NPD5125	Phase 3
0.7037	Intermediate Similarity	NPD5126	Approved
0.7037	Intermediate Similarity	NPD5844	Phase 1
0.7034	Intermediate Similarity	NPD5588	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