NPASS Compound

Structure

NPC71610 OpenBabel07101718322D 23 25 0 0 1 0 0 0 0 0999 V2000 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 -1.0000 -0.0000 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 3.4641 -0.0000 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 -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 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 2.5981 -0.5000 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 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 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 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 1 12 1 0 0 0 0 2 12 1 0 0 0 0 5 8 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 19 3 1 1 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	341.995
LogP:	3.197
LogD:	2.901
LogS:	-3.761
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.879
Synthetic Accessibility Score:	4.097
Fsp3:	0.55
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:	-4.732
MDCK Permeability:	3.0913932278053835e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.668

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	96.36569213867188%
Volume Distribution (VD):	0.592
Pgp-substrate:	4.08448600769043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.116
CYP1A2-substrate:	0.761
CYP2C19-inhibitor:	0.173
CYP2C19-substrate:	0.809
CYP2C9-inhibitor:	0.298
CYP2C9-substrate:	0.622
CYP2D6-inhibitor:	0.387
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.825
CYP3A4-substrate:	0.815

ADMET: Excretion

Clearance (CL):	11.673
Half-life (T1/2):	0.353

ADMET: Toxicity

hERG Blockers:	0.275
Human Hepatotoxicity (H-HT):	0.344
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.143
Rat Oral Acute Toxicity:	0.472
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.65
Carcinogencity:	0.807
Eye Corrosion:	0.004
Eye Irritation:	0.027
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC71610

Natural Product ID:	NPC71610
*Common Name:**	Trogopteroid G
IUPAC Name:	(1S,4aS,10aR)-7-hydroxy-1-(hydroxymethyl)-1,4a-dimethyl-8-propan-2-yl-10,10a-dihydro-9H-phenanthren-2-one
Synonyms:	Trogopteroid G
Standard InCHIKey:	FPNBOQARUCJXBH-NSISKUIASA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-12(2)18-13-5-8-16-19(3,14(13)6-7-15(18)22)10-9-17(23)20(16,4)11-21/h6-7,9-10,12,16,21-22H,5,8,11H2,1-4H3/t16-,19-,20-/m1/s1
SMILES:	CC(C)c1c2CC[C@@H]3[C@](C)(C=CC(=O)[C@]3(C)CO)c2ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095397
PubChem CID:	46833409
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003027] 3-hydroxysteroids

*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
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	feces	n.a.	n.a.	PMID[20402524]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO882	Trogopterus xanthipes	Species	Sciuridae	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
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	40000.0	nM	PMID[565954]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[565954]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	40000.0	nM	PMID[565954]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	40000.0	nM	PMID[565954]

☑ 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 NPC71610 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	261
0.1-0.2	1411
0.2-0.3	2838
0.3-0.4	7508
0.4-0.5	11030
0.5-0.6	7715
0.6-0.7	9314
0.7-0.8	2370
0.8-0.85	207
0.85-0.9	40
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC198014
0.9256	High Similarity	NPC154696
0.9174	High Similarity	NPC259703
0.9174	High Similarity	NPC32322
0.9113	High Similarity	NPC87985
0.9106	High Similarity	NPC471187
0.9098	High Similarity	NPC253627
0.9032	High Similarity	NPC181334
0.8984	High Similarity	NPC471851
0.8968	High Similarity	NPC72667
0.8889	High Similarity	NPC254492
0.8871	High Similarity	NPC11250
0.8846	High Similarity	NPC78307
0.8828	High Similarity	NPC171460
0.8819	High Similarity	NPC69424
0.8819	High Similarity	NPC78364
0.8819	High Similarity	NPC84672
0.8819	High Similarity	NPC176130
0.8779	High Similarity	NPC202225
0.8769	High Similarity	NPC165612
0.875	High Similarity	NPC3009
0.875	High Similarity	NPC96024
0.875	High Similarity	NPC268160
0.873	High Similarity	NPC199273
0.872	High Similarity	NPC176208
0.872	High Similarity	NPC121168
0.871	High Similarity	NPC241001
0.8702	High Similarity	NPC477139
0.8692	High Similarity	NPC476847
0.8689	High Similarity	NPC477136
0.8682	High Similarity	NPC303910
0.8682	High Similarity	NPC276238
0.8678	High Similarity	NPC147179
0.8672	High Similarity	NPC471530
0.8661	High Similarity	NPC137750
0.864	High Similarity	NPC249340
0.864	High Similarity	NPC162935
0.8629	High Similarity	NPC318552
0.8629	High Similarity	NPC190501
0.8615	High Similarity	NPC108129
0.8607	High Similarity	NPC219112
0.8607	High Similarity	NPC308828
0.8583	High Similarity	NPC234890
0.8583	High Similarity	NPC74507
0.8582	High Similarity	NPC475957
0.8571	High Similarity	NPC282577
0.8561	High Similarity	NPC475627
0.8561	High Similarity	NPC475457
0.8561	High Similarity	NPC475346
0.8561	High Similarity	NPC18982
0.855	High Similarity	NPC244699
0.8548	High Similarity	NPC42657
0.8538	High Similarity	NPC131684
0.8527	High Similarity	NPC30491
0.8527	High Similarity	NPC262936
0.8525	High Similarity	NPC192948
0.8525	High Similarity	NPC35797
0.848	Intermediate Similarity	NPC478121
0.8478	Intermediate Similarity	NPC199936
0.8468	Intermediate Similarity	NPC469609
0.8462	Intermediate Similarity	NPC48248
0.8455	Intermediate Similarity	NPC477137
0.8455	Intermediate Similarity	NPC308311
0.8455	Intermediate Similarity	NPC38893
0.845	Intermediate Similarity	NPC3224
0.8438	Intermediate Similarity	NPC68756
0.8438	Intermediate Similarity	NPC152525
0.8433	Intermediate Similarity	NPC283088
0.843	Intermediate Similarity	NPC250323
0.8425	Intermediate Similarity	NPC307174
0.8421	Intermediate Similarity	NPC53896
0.8421	Intermediate Similarity	NPC52407
0.8421	Intermediate Similarity	NPC138472
0.8417	Intermediate Similarity	NPC141782
0.8417	Intermediate Similarity	NPC13482
0.8409	Intermediate Similarity	NPC85342
0.8406	Intermediate Similarity	NPC477209
0.84	Intermediate Similarity	NPC182240
0.84	Intermediate Similarity	NPC473974
0.84	Intermediate Similarity	NPC258366
0.84	Intermediate Similarity	NPC31296
0.84	Intermediate Similarity	NPC79933
0.8397	Intermediate Similarity	NPC146647
0.8397	Intermediate Similarity	NPC25736
0.8397	Intermediate Similarity	NPC34414
0.8397	Intermediate Similarity	NPC117899
0.8397	Intermediate Similarity	NPC99731
0.8387	Intermediate Similarity	NPC304510
0.8387	Intermediate Similarity	NPC172219
0.8372	Intermediate Similarity	NPC123506
0.8359	Intermediate Similarity	NPC273683
0.8358	Intermediate Similarity	NPC50924
0.8346	Intermediate Similarity	NPC58685
0.8346	Intermediate Similarity	NPC246693
0.8346	Intermediate Similarity	NPC242358
0.8346	Intermediate Similarity	NPC110609
0.8345	Intermediate Similarity	NPC478164
0.8333	Intermediate Similarity	NPC285829
0.8333	Intermediate Similarity	NPC199253
0.8333	Intermediate Similarity	NPC206778
0.8333	Intermediate Similarity	NPC136588
0.8321	Intermediate Similarity	NPC193203
0.832	Intermediate Similarity	NPC154030
0.832	Intermediate Similarity	NPC471671
0.8309	Intermediate Similarity	NPC53001
0.8308	Intermediate Similarity	NPC306765
0.8308	Intermediate Similarity	NPC269598
0.8306	Intermediate Similarity	NPC477453
0.8306	Intermediate Similarity	NPC92
0.8306	Intermediate Similarity	NPC469663
0.8296	Intermediate Similarity	NPC103082
0.8295	Intermediate Similarity	NPC142956
0.8295	Intermediate Similarity	NPC75432
0.8295	Intermediate Similarity	NPC474766
0.8295	Intermediate Similarity	NPC173978
0.8293	Intermediate Similarity	NPC285350
0.8284	Intermediate Similarity	NPC115458
0.8284	Intermediate Similarity	NPC111845
0.8284	Intermediate Similarity	NPC314048
0.8281	Intermediate Similarity	NPC300274
0.8281	Intermediate Similarity	NPC164947
0.8279	Intermediate Similarity	NPC228425
0.8273	Intermediate Similarity	NPC469855
0.8273	Intermediate Similarity	NPC471972
0.8273	Intermediate Similarity	NPC469520
0.8273	Intermediate Similarity	NPC471971
0.8273	Intermediate Similarity	NPC30846
0.8273	Intermediate Similarity	NPC308572
0.8271	Intermediate Similarity	NPC93015
0.8271	Intermediate Similarity	NPC17083
0.8271	Intermediate Similarity	NPC72669
0.8271	Intermediate Similarity	NPC18798
0.8271	Intermediate Similarity	NPC41847
0.8271	Intermediate Similarity	NPC474517
0.8268	Intermediate Similarity	NPC164852
0.8261	Intermediate Similarity	NPC472801
0.8261	Intermediate Similarity	NPC471853
0.8258	Intermediate Similarity	NPC474546
0.8254	Intermediate Similarity	NPC469644
0.8248	Intermediate Similarity	NPC87723
0.8235	Intermediate Similarity	NPC249817
0.8235	Intermediate Similarity	NPC474311
0.8235	Intermediate Similarity	NPC193358
0.8235	Intermediate Similarity	NPC7464
0.8235	Intermediate Similarity	NPC471670
0.8231	Intermediate Similarity	NPC137416
0.8227	Intermediate Similarity	NPC478160
0.8226	Intermediate Similarity	NPC23402
0.8222	Intermediate Similarity	NPC12070
0.8222	Intermediate Similarity	NPC194970
0.8217	Intermediate Similarity	NPC135062
0.8217	Intermediate Similarity	NPC275145
0.8217	Intermediate Similarity	NPC375356
0.8209	Intermediate Similarity	NPC70622
0.8201	Intermediate Similarity	NPC106519
0.8201	Intermediate Similarity	NPC91019
0.8197	Intermediate Similarity	NPC260323
0.8197	Intermediate Similarity	NPC176279
0.8195	Intermediate Similarity	NPC55949
0.8195	Intermediate Similarity	NPC253488
0.8195	Intermediate Similarity	NPC31799
0.8189	Intermediate Similarity	NPC135467
0.8189	Intermediate Similarity	NPC260832
0.8189	Intermediate Similarity	NPC7151
0.8189	Intermediate Similarity	NPC473662
0.8189	Intermediate Similarity	NPC216297
0.8182	Intermediate Similarity	NPC282923
0.8182	Intermediate Similarity	NPC229894
0.8175	Intermediate Similarity	NPC36868
0.8175	Intermediate Similarity	NPC475482
0.8175	Intermediate Similarity	NPC216940
0.8175	Intermediate Similarity	NPC277559
0.8175	Intermediate Similarity	NPC41567
0.8175	Intermediate Similarity	NPC198621
0.8175	Intermediate Similarity	NPC305060
0.8175	Intermediate Similarity	NPC22676
0.8175	Intermediate Similarity	NPC477592
0.8175	Intermediate Similarity	NPC471152
0.8169	Intermediate Similarity	NPC143685
0.8168	Intermediate Similarity	NPC49647
0.8168	Intermediate Similarity	NPC136342
0.8168	Intermediate Similarity	NPC295202
0.8168	Intermediate Similarity	NPC227741
0.8167	Intermediate Similarity	NPC228737
0.8162	Intermediate Similarity	NPC153088
0.8162	Intermediate Similarity	NPC249272
0.8162	Intermediate Similarity	NPC472804
0.8162	Intermediate Similarity	NPC173569
0.8162	Intermediate Similarity	NPC477874
0.816	Intermediate Similarity	NPC471668
0.8156	Intermediate Similarity	NPC469856
0.8156	Intermediate Similarity	NPC469854
0.8154	Intermediate Similarity	NPC15127
0.8148	Intermediate Similarity	NPC476282
0.8148	Intermediate Similarity	NPC114183
0.8148	Intermediate Similarity	NPC49742
0.8145	Intermediate Similarity	NPC195922
0.8143	Intermediate Similarity	NPC135524
0.8143	Intermediate Similarity	NPC85310
0.8143	Intermediate Similarity	NPC248068

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 NPC71610 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	974
0.2-0.3	1377
0.3-0.4	2588
0.4-0.5	2162
0.5-0.6	1230
0.6-0.7	492
0.7-0.8	56
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
0.878	High Similarity	NPD2932	Approved
0.8629	High Similarity	NPD3019	Approved
0.8203	Intermediate Similarity	NPD1201	Approved
0.8092	Intermediate Similarity	NPD1470	Approved
0.8031	Intermediate Similarity	NPD3091	Approved
0.8016	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6663	Approved
0.7984	Intermediate Similarity	NPD3026	Approved
0.7984	Intermediate Similarity	NPD3023	Approved
0.797	Intermediate Similarity	NPD5736	Approved
0.7969	Intermediate Similarity	NPD3025	Approved
0.7969	Intermediate Similarity	NPD3024	Approved
0.7943	Intermediate Similarity	NPD8166	Discontinued
0.7842	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD5406	Approved
0.7786	Intermediate Similarity	NPD5404	Approved
0.7786	Intermediate Similarity	NPD5408	Approved
0.7786	Intermediate Similarity	NPD3092	Approved
0.7786	Intermediate Similarity	NPD5405	Approved
0.7714	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7003	Approved
0.7634	Intermediate Similarity	NPD3095	Discontinued
0.7603	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD7635	Approved
0.7557	Intermediate Similarity	NPD1651	Approved
0.7556	Intermediate Similarity	NPD1164	Approved
0.7556	Intermediate Similarity	NPD3094	Phase 2
0.7535	Intermediate Similarity	NPD2935	Discontinued
0.7534	Intermediate Similarity	NPD7390	Discontinued
0.7517	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD4059	Approved
0.7481	Intermediate Similarity	NPD1283	Approved
0.7466	Intermediate Similarity	NPD3300	Phase 2
0.7442	Intermediate Similarity	NPD5951	Approved
0.744	Intermediate Similarity	NPD2342	Discontinued
0.7438	Intermediate Similarity	NPD3020	Approved
0.7432	Intermediate Similarity	NPD6273	Approved
0.7372	Intermediate Similarity	NPD2798	Approved
0.7368	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2346	Discontinued
0.7343	Intermediate Similarity	NPD2799	Discontinued
0.7333	Intermediate Similarity	NPD1809	Phase 2
0.7293	Intermediate Similarity	NPD5691	Approved
0.7285	Intermediate Similarity	NPD7458	Discontinued
0.7279	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD288	Approved
0.7259	Intermediate Similarity	NPD1281	Approved
0.725	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8032	Phase 2
0.7211	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7819	Suspended
0.7206	Intermediate Similarity	NPD3972	Approved
0.7194	Intermediate Similarity	NPD4208	Discontinued
0.719	Intermediate Similarity	NPD844	Approved
0.719	Intermediate Similarity	NPD2860	Approved
0.719	Intermediate Similarity	NPD2859	Approved
0.7188	Intermediate Similarity	NPD3021	Approved
0.7188	Intermediate Similarity	NPD4750	Phase 3
0.7188	Intermediate Similarity	NPD3022	Approved
0.7183	Intermediate Similarity	NPD4060	Phase 1
0.7183	Intermediate Similarity	NPD4140	Approved
0.7183	Intermediate Similarity	NPD943	Approved
0.7172	Intermediate Similarity	NPD6099	Approved
0.7172	Intermediate Similarity	NPD6100	Approved
0.7171	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD845	Approved
0.7132	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1751	Approved
0.7109	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2933	Approved
0.7107	Intermediate Similarity	NPD2934	Approved
0.7103	Intermediate Similarity	NPD1510	Phase 2
0.7101	Intermediate Similarity	NPD1876	Approved
0.7083	Intermediate Similarity	NPD1607	Approved
0.7083	Intermediate Similarity	NPD4097	Suspended
0.7077	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9493	Approved
0.7063	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2979	Phase 3
0.7063	Intermediate Similarity	NPD3620	Phase 2
0.7063	Intermediate Similarity	NPD1240	Approved
0.7059	Intermediate Similarity	NPD3226	Approved
0.705	Intermediate Similarity	NPD2797	Approved
0.7045	Intermediate Similarity	NPD2629	Approved
0.7044	Intermediate Similarity	NPD6959	Discontinued
0.7042	Intermediate Similarity	NPD3764	Approved
0.7037	Intermediate Similarity	NPD4093	Discontinued
0.7029	Intermediate Similarity	NPD1755	Approved
0.7027	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7028	Phase 2
0.7013	Intermediate Similarity	NPD4380	Phase 2
0.7007	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2344	Approved
0.7	Intermediate Similarity	NPD4624	Approved
0.7	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7743	Approved
0.6986	Remote Similarity	NPD7742	Approved
0.6985	Remote Similarity	NPD2286	Discontinued
0.698	Remote Similarity	NPD4628	Phase 3
0.698	Remote Similarity	NPD3750	Approved
0.698	Remote Similarity	NPD3400	Discontinued
0.6977	Remote Similarity	NPD74	Approved
0.6977	Remote Similarity	NPD9266	Approved
0.6975	Remote Similarity	NPD7473	Discontinued
0.6972	Remote Similarity	NPD7008	Discontinued
0.6972	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1241	Discontinued
0.697	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6651	Approved
0.6959	Remote Similarity	NPD970	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3636	Approved
0.695	Remote Similarity	NPD3637	Approved
0.695	Remote Similarity	NPD3635	Approved
0.6943	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4476	Approved
0.6939	Remote Similarity	NPD4477	Approved
0.6929	Remote Similarity	NPD1237	Approved
0.6923	Remote Similarity	NPD2313	Discontinued
0.6923	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2532	Approved
0.6908	Remote Similarity	NPD2534	Approved
0.6908	Remote Similarity	NPD2533	Approved
0.6906	Remote Similarity	NPD5327	Phase 3
0.6906	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4207	Discontinued
0.6901	Remote Similarity	NPD2606	Approved
0.6901	Remote Similarity	NPD2605	Approved
0.6899	Remote Similarity	NPD9264	Approved
0.6899	Remote Similarity	NPD9267	Approved
0.6899	Remote Similarity	NPD9263	Approved
0.6897	Remote Similarity	NPD5735	Approved
0.6894	Remote Similarity	NPD6232	Discontinued
0.6884	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.688	Remote Similarity	NPD2066	Phase 3
0.6879	Remote Similarity	NPD2195	Approved
0.6879	Remote Similarity	NPD2194	Approved
0.6866	Remote Similarity	NPD3317	Approved
0.6861	Remote Similarity	NPD4589	Approved
0.6855	Remote Similarity	NPD3495	Discontinued
0.6853	Remote Similarity	NPD5156	Approved
0.6853	Remote Similarity	NPD5155	Approved
0.685	Remote Similarity	NPD1930	Approved
0.685	Remote Similarity	NPD1929	Approved
0.685	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1549	Phase 2
0.6842	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD9545	Approved
0.6835	Remote Similarity	NPD4878	Approved
0.6835	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD8127	Discontinued
0.6824	Remote Similarity	NPD2531	Phase 2
0.6824	Remote Similarity	NPD2438	Suspended
0.6824	Remote Similarity	NPD2796	Approved
0.6821	Remote Similarity	NPD2309	Approved
0.6815	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2800	Approved
0.68	Remote Similarity	NPD3638	Discontinued
0.6797	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1792	Phase 2
0.6792	Remote Similarity	NPD7768	Phase 2
0.6786	Remote Similarity	NPD5035	Approved
0.6786	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3595	Approved
0.6783	Remote Similarity	NPD3594	Approved
0.6781	Remote Similarity	NPD6355	Discontinued
0.6779	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7236	Approved
0.6772	Remote Similarity	NPD940	Approved
0.6772	Remote Similarity	NPD846	Approved
0.6769	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7610	Discontinued
0.6765	Remote Similarity	NPD8150	Discontinued
0.6755	Remote Similarity	NPD4110	Phase 3
0.6755	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7411	Suspended
0.675	Remote Similarity	NPD7075	Discontinued
0.6747	Remote Similarity	NPD4956	Approved
0.6739	Remote Similarity	NPD1778	Approved
0.6738	Remote Similarity	NPD6696	Suspended
0.6736	Remote Similarity	NPD4625	Phase 3
0.6735	Remote Similarity	NPD6353	Approved
0.6726	Remote Similarity	NPD4955	Approved
0.6726	Remote Similarity	NPD5034	Approved
0.6726	Remote Similarity	NPD4954	Approved
0.6726	Remote Similarity	NPD5028	Approved
0.6726	Remote Similarity	NPD5026	Approved
0.6726	Remote Similarity	NPD36	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