NPASS Compound

Structure

NPC469663 OpenBabel07101718222D 23 25 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 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 -0.3660 2.3660 0.0000 C 0 0 0 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 -1.7321 -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 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 -0.8660 -0.5000 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 -1.3660 2.3660 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 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 0 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 2.5981 -0.5000 0.0000 C 0 0 0 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 -0.8660 1.5000 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 -2.3660 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 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 12 1 0 0 0 0 2 12 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 13 17 2 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 22 1 6 0 0 0 17 23 1 0 0 0 0 18 19 1 6 0 0 0 18 20 1 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:	318.22
Volume:	347.268
LogP:	3.568
LogD:	2.919
LogS:	-3.526
# Rotatable Bonds:	2
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.782
Synthetic Accessibility Score:	4.225
Fsp3:	0.7
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:	-4.651
MDCK Permeability:	1.3916985153628048e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.3
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.817
30% Bioavailability (F30%):	0.891

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.357
Plasma Protein Binding (PPB):	94.19969940185547%
Volume Distribution (VD):	2.577
Pgp-substrate:	8.021097183227539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.816
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.495
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.219
CYP3A4-inhibitor:	0.806
CYP3A4-substrate:	0.535

ADMET: Excretion

Clearance (CL):	13.631
Half-life (T1/2):	0.303

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.259
Maximum Recommended Daily Dose:	0.183
Skin Sensitization:	0.851
Carcinogencity:	0.108
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.742

Download Data

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

Natural Product: NPC469663

Natural Product ID:	NPC469663
*Common Name:**	Macrophynin E
IUPAC Name:	(4bS,8S,8aR,9R)-8-(hydroxymethyl)-4b,8-dimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthrene-1,9-diol
Synonyms:	Macrophynin E
Standard InCHIKey:	COPQDCGDRVTCTF-GSEOLPGOSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-12(2)13-6-7-15-14(17(13)23)10-16(22)18-19(3,11-21)8-5-9-20(15,18)4/h6-7,12,16,18,21-23H,5,8-11H2,1-4H3/t16-,18+,19-,20-/m1/s1
SMILES:	CC(C)C1=C(C2=C(C=C1)C3(CCCC(C3C(C2)O)(C)CO)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097039
PubChem CID:	46887227
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
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[488246]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[488246]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	40000.0	nM	PMID[488246]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	40000.0	nM	PMID[488246]

☑ 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 NPC469663 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	272
0.1-0.2	1402
0.2-0.3	2714
0.3-0.4	8583
0.4-0.5	10887
0.5-0.6	10954
0.6-0.7	6264
0.7-0.8	1359
0.8-0.85	158
0.85-0.9	72
0.9-0.95	18
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC92
0.9636	High Similarity	NPC219112
0.9636	High Similarity	NPC38893
0.9636	High Similarity	NPC308311
0.9636	High Similarity	NPC477137
0.9636	High Similarity	NPC308828
0.9554	High Similarity	NPC469644
0.955	High Similarity	NPC477136
0.9545	High Similarity	NPC192948
0.9545	High Similarity	NPC147179
0.9545	High Similarity	NPC35797
0.9464	High Similarity	NPC469609
0.9464	High Similarity	NPC471671
0.9455	High Similarity	NPC268160
0.9375	High Similarity	NPC304510
0.9375	High Similarity	NPC172219
0.9266	High Similarity	NPC132720
0.9182	High Similarity	NPC176279
0.9182	High Similarity	NPC260323
0.913	High Similarity	NPC260832
0.913	High Similarity	NPC135467
0.9123	High Similarity	NPC154030
0.9107	High Similarity	NPC195922
0.9099	High Similarity	NPC228425
0.9099	High Similarity	NPC250323
0.9091	High Similarity	NPC141782
0.9027	High Similarity	NPC469719
0.9009	High Similarity	NPC77772
0.8991	High Similarity	NPC472979
0.8991	High Similarity	NPC27252
0.8983	High Similarity	NPC471187
0.8981	High Similarity	NPC243601
0.8957	High Similarity	NPC164649
0.8957	High Similarity	NPC48342
0.8947	High Similarity	NPC471668
0.8929	High Similarity	NPC46940
0.8919	High Similarity	NPC13482
0.8909	High Similarity	NPC149455
0.8909	High Similarity	NPC64642
0.8909	High Similarity	NPC472982
0.8908	High Similarity	NPC181334
0.8898	High Similarity	NPC471794
0.8889	High Similarity	NPC328504
0.8879	High Similarity	NPC151197
0.885	High Similarity	NPC715
0.8839	High Similarity	NPC470770
0.8839	High Similarity	NPC95716
0.8839	High Similarity	NPC266937
0.8818	High Similarity	NPC151477
0.8818	High Similarity	NPC472980
0.8807	High Similarity	NPC117115
0.8783	High Similarity	NPC257540
0.8783	High Similarity	NPC141001
0.8783	High Similarity	NPC474358
0.8783	High Similarity	NPC137496
0.8783	High Similarity	NPC247858
0.8783	High Similarity	NPC474387
0.8783	High Similarity	NPC154511
0.8772	High Similarity	NPC471534
0.8761	High Similarity	NPC302371
0.8761	High Similarity	NPC177962
0.8761	High Similarity	NPC62867
0.8739	High Similarity	NPC11250
0.8739	High Similarity	NPC11554
0.8739	High Similarity	NPC152946
0.8739	High Similarity	NPC478058
0.8739	High Similarity	NPC71094
0.8718	High Similarity	NPC323074
0.8718	High Similarity	NPC126002
0.8718	High Similarity	NPC93071
0.8716	High Similarity	NPC475225
0.8707	High Similarity	NPC16030
0.8689	High Similarity	NPC471077
0.8678	High Similarity	NPC87985
0.8678	High Similarity	NPC76119
0.8678	High Similarity	NPC4286
0.8673	High Similarity	NPC322753
0.8667	High Similarity	NPC198014
0.8661	High Similarity	NPC58865
0.8655	High Similarity	NPC142198
0.8655	High Similarity	NPC253627
0.8655	High Similarity	NPC77569
0.8649	High Similarity	NPC320439
0.8644	High Similarity	NPC477037
0.8644	High Similarity	NPC318581
0.8644	High Similarity	NPC325544
0.8624	High Similarity	NPC471228
0.8624	High Similarity	NPC235762
0.8624	High Similarity	NPC19856
0.8607	High Similarity	NPC321822
0.8607	High Similarity	NPC325294
0.8571	High Similarity	NPC32322
0.8571	High Similarity	NPC259703
0.8571	High Similarity	NPC262365
0.856	High Similarity	NPC476847
0.856	High Similarity	NPC312341
0.8559	High Similarity	NPC21594
0.8547	High Similarity	NPC299180
0.8545	High Similarity	NPC238696
0.8525	High Similarity	NPC137750
0.8525	High Similarity	NPC124030
0.8522	High Similarity	NPC317869
0.8509	High Similarity	NPC151537
0.85	High Similarity	NPC162935
0.85	High Similarity	NPC249340
0.8496	Intermediate Similarity	NPC314187
0.8492	Intermediate Similarity	NPC85595
0.8487	Intermediate Similarity	NPC68339
0.8482	Intermediate Similarity	NPC66834
0.848	Intermediate Similarity	NPC196193
0.8475	Intermediate Similarity	NPC206
0.8468	Intermediate Similarity	NPC47284
0.8455	Intermediate Similarity	NPC100414
0.8455	Intermediate Similarity	NPC43000
0.844	Intermediate Similarity	NPC174911
0.8435	Intermediate Similarity	NPC471179
0.843	Intermediate Similarity	NPC176208
0.843	Intermediate Similarity	NPC121168
0.843	Intermediate Similarity	NPC321402
0.8421	Intermediate Similarity	NPC296683
0.8417	Intermediate Similarity	NPC241001
0.8413	Intermediate Similarity	NPC471851
0.8393	Intermediate Similarity	NPC271274
0.8393	Intermediate Similarity	NPC53740
0.8387	Intermediate Similarity	NPC186889
0.8387	Intermediate Similarity	NPC476536
0.8387	Intermediate Similarity	NPC108164
0.8378	Intermediate Similarity	NPC272029
0.8378	Intermediate Similarity	NPC323810
0.8376	Intermediate Similarity	NPC474486
0.8376	Intermediate Similarity	NPC84999
0.8376	Intermediate Similarity	NPC246760
0.8364	Intermediate Similarity	NPC252105
0.8364	Intermediate Similarity	NPC51015
0.8362	Intermediate Similarity	NPC322239
0.8349	Intermediate Similarity	NPC33675
0.8349	Intermediate Similarity	NPC299762
0.8348	Intermediate Similarity	NPC308689
0.8348	Intermediate Similarity	NPC469912
0.8347	Intermediate Similarity	NPC475166
0.8347	Intermediate Similarity	NPC154696
0.8346	Intermediate Similarity	NPC59239
0.8333	Intermediate Similarity	NPC99795
0.8333	Intermediate Similarity	NPC324602
0.8306	Intermediate Similarity	NPC71610
0.8305	Intermediate Similarity	NPC472862
0.8304	Intermediate Similarity	NPC138942
0.8291	Intermediate Similarity	NPC249270
0.8291	Intermediate Similarity	NPC12656
0.8288	Intermediate Similarity	NPC269212
0.8281	Intermediate Similarity	NPC227719
0.8281	Intermediate Similarity	NPC78307
0.8276	Intermediate Similarity	NPC228452
0.8273	Intermediate Similarity	NPC72729
0.8273	Intermediate Similarity	NPC211885
0.8273	Intermediate Similarity	NPC294741
0.8273	Intermediate Similarity	NPC225506
0.8268	Intermediate Similarity	NPC78575
0.8264	Intermediate Similarity	NPC129176
0.8261	Intermediate Similarity	NPC44732
0.8257	Intermediate Similarity	NPC79241
0.8257	Intermediate Similarity	NPC6597
0.8257	Intermediate Similarity	NPC474073
0.825	Intermediate Similarity	NPC42657
0.824	Intermediate Similarity	NPC30491
0.824	Intermediate Similarity	NPC262936
0.8235	Intermediate Similarity	NPC320864
0.8231	Intermediate Similarity	NPC68292
0.823	Intermediate Similarity	NPC155072
0.8217	Intermediate Similarity	NPC202225
0.8214	Intermediate Similarity	NPC288411
0.8205	Intermediate Similarity	NPC319803
0.8203	Intermediate Similarity	NPC289624
0.8203	Intermediate Similarity	NPC27578
0.8203	Intermediate Similarity	NPC321086
0.8197	Intermediate Similarity	NPC474115
0.819	Intermediate Similarity	NPC471188
0.8189	Intermediate Similarity	NPC472793
0.8182	Intermediate Similarity	NPC103916
0.8182	Intermediate Similarity	NPC122005
0.8182	Intermediate Similarity	NPC478121
0.8182	Intermediate Similarity	NPC128723
0.8182	Intermediate Similarity	NPC318552
0.8182	Intermediate Similarity	NPC99734
0.8182	Intermediate Similarity	NPC190501
0.8182	Intermediate Similarity	NPC252821
0.8175	Intermediate Similarity	NPC201069
0.8167	Intermediate Similarity	NPC48781
0.8167	Intermediate Similarity	NPC9592
0.8165	Intermediate Similarity	NPC312132
0.8165	Intermediate Similarity	NPC259512
0.816	Intermediate Similarity	NPC470724
0.8158	Intermediate Similarity	NPC474352
0.8151	Intermediate Similarity	NPC312105
0.8148	Intermediate Similarity	NPC289769
0.8142	Intermediate Similarity	NPC219286
0.8142	Intermediate Similarity	NPC471350
0.8142	Intermediate Similarity	NPC99557
0.8136	Intermediate Similarity	NPC473137
0.8136	Intermediate Similarity	NPC107240

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 NPC469663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	891
0.2-0.3	1263
0.3-0.4	2815
0.4-0.5	2089
0.5-0.6	1291
0.6-0.7	429
0.7-0.8	91
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8957	High Similarity	NPD3091	Approved
0.8761	High Similarity	NPD7635	Approved
0.8655	High Similarity	NPD3092	Approved
0.8649	High Similarity	NPD2342	Discontinued
0.8525	High Similarity	NPD3094	Phase 2
0.8487	Intermediate Similarity	NPD3095	Discontinued
0.8182	Intermediate Similarity	NPD3019	Approved
0.8182	Intermediate Similarity	NPD4059	Approved
0.8165	Intermediate Similarity	NPD288	Approved
0.8108	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5736	Approved
0.8073	Intermediate Similarity	NPD844	Approved
0.8073	Intermediate Similarity	NPD1809	Phase 2
0.8056	Intermediate Similarity	NPD845	Approved
0.8033	Intermediate Similarity	NPD2932	Approved
0.8018	Intermediate Similarity	NPD3020	Approved
0.7965	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD4750	Phase 3
0.7846	Intermediate Similarity	NPD6663	Approved
0.7818	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD4097	Suspended
0.7786	Intermediate Similarity	NPD3620	Phase 2
0.7786	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD2859	Approved
0.7748	Intermediate Similarity	NPD2860	Approved
0.7742	Intermediate Similarity	NPD2286	Discontinued
0.7731	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3021	Approved
0.7712	Intermediate Similarity	NPD3022	Approved
0.7705	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD7743	Approved
0.7687	Intermediate Similarity	NPD7742	Approved
0.7661	Intermediate Similarity	NPD4093	Discontinued
0.7658	Intermediate Similarity	NPD2933	Approved
0.7658	Intermediate Similarity	NPD2934	Approved
0.7652	Intermediate Similarity	NPD4140	Approved
0.7638	Intermediate Similarity	NPD5327	Phase 3
0.76	Intermediate Similarity	NPD4626	Approved
0.76	Intermediate Similarity	NPD1751	Approved
0.7597	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4624	Approved
0.7594	Intermediate Similarity	NPD5735	Approved
0.7541	Intermediate Similarity	NPD497	Approved
0.754	Intermediate Similarity	NPD3023	Approved
0.754	Intermediate Similarity	NPD3026	Approved
0.752	Intermediate Similarity	NPD3025	Approved
0.752	Intermediate Similarity	NPD3024	Approved
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2605	Approved
0.7481	Intermediate Similarity	NPD2606	Approved
0.7464	Intermediate Similarity	NPD3638	Discontinued
0.7459	Intermediate Similarity	NPD495	Approved
0.7459	Intermediate Similarity	NPD498	Approved
0.7459	Intermediate Similarity	NPD496	Approved
0.7442	Intermediate Similarity	NPD6696	Suspended
0.7424	Intermediate Similarity	NPD4625	Phase 3
0.7424	Intermediate Similarity	NPD5155	Approved
0.7424	Intermediate Similarity	NPD5156	Approved
0.7419	Intermediate Similarity	NPD7340	Approved
0.7417	Intermediate Similarity	NPD1792	Phase 2
0.7407	Intermediate Similarity	NPD6353	Approved
0.7405	Intermediate Similarity	NPD3635	Approved
0.7405	Intermediate Similarity	NPD3636	Approved
0.7405	Intermediate Similarity	NPD2861	Phase 2
0.7405	Intermediate Similarity	NPD3637	Approved
0.7388	Intermediate Similarity	NPD4060	Phase 1
0.7381	Intermediate Similarity	NPD5691	Approved
0.7357	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD3594	Approved
0.7348	Intermediate Similarity	NPD3595	Approved
0.7344	Intermediate Similarity	NPD1201	Approved
0.7338	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD2194	Approved
0.7328	Intermediate Similarity	NPD2195	Approved
0.7323	Intermediate Similarity	NPD4589	Approved
0.7317	Intermediate Similarity	NPD1398	Phase 1
0.7302	Intermediate Similarity	NPD7741	Discontinued
0.7265	Intermediate Similarity	NPD846	Approved
0.7265	Intermediate Similarity	NPD940	Approved
0.7239	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6674	Discontinued
0.7203	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6671	Approved
0.7188	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD2229	Approved
0.7177	Intermediate Similarity	NPD2234	Approved
0.7177	Intermediate Similarity	NPD2228	Approved
0.7176	Intermediate Similarity	NPD1283	Approved
0.7167	Intermediate Similarity	NPD1444	Approved
0.7167	Intermediate Similarity	NPD1445	Approved
0.7165	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7330	Discontinued
0.7165	Intermediate Similarity	NPD5303	Approved
0.7165	Intermediate Similarity	NPD5304	Approved
0.7163	Intermediate Similarity	NPD7003	Approved
0.7154	Intermediate Similarity	NPD2232	Approved
0.7154	Intermediate Similarity	NPD2233	Approved
0.7154	Intermediate Similarity	NPD2230	Approved
0.7133	Intermediate Similarity	NPD7041	Phase 2
0.7133	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2238	Phase 2
0.7122	Intermediate Similarity	NPD5405	Approved
0.7122	Intermediate Similarity	NPD5406	Approved
0.7122	Intermediate Similarity	NPD5404	Approved
0.7122	Intermediate Similarity	NPD5408	Approved
0.7121	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1470	Approved
0.712	Intermediate Similarity	NPD5951	Approved
0.7109	Intermediate Similarity	NPD1651	Approved
0.7101	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4749	Approved
0.709	Intermediate Similarity	NPD4908	Phase 1
0.7083	Intermediate Similarity	NPD3645	Discontinued
0.7071	Intermediate Similarity	NPD4725	Approved
0.7071	Intermediate Similarity	NPD4721	Approved
0.7071	Intermediate Similarity	NPD4726	Approved
0.7054	Intermediate Similarity	NPD5125	Phase 3
0.7054	Intermediate Similarity	NPD5126	Approved
0.7054	Intermediate Similarity	NPD7725	Approved
0.705	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD8166	Discontinued
0.7034	Intermediate Similarity	NPD1242	Phase 1
0.7	Intermediate Similarity	NPD111	Approved
0.6984	Remote Similarity	NPD9618	Approved
0.6984	Remote Similarity	NPD9614	Approved
0.6984	Remote Similarity	NPD2629	Approved
0.6977	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4659	Approved
0.6957	Remote Similarity	NPD3657	Discovery
0.695	Remote Similarity	NPD5763	Approved
0.695	Remote Similarity	NPD5762	Approved
0.695	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1281	Approved
0.6947	Remote Similarity	NPD1611	Approved
0.6947	Remote Similarity	NPD1610	Phase 2
0.694	Remote Similarity	NPD6584	Phase 3
0.6929	Remote Similarity	NPD4198	Discontinued
0.6929	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7157	Approved
0.6918	Remote Similarity	NPD6273	Approved
0.6917	Remote Similarity	NPD8651	Approved
0.6912	Remote Similarity	NPD3027	Phase 3
0.6905	Remote Similarity	NPD5283	Phase 1
0.6901	Remote Similarity	NPD7037	Approved
0.6899	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7390	Discontinued
0.6894	Remote Similarity	NPD2231	Phase 2
0.6894	Remote Similarity	NPD2235	Phase 2
0.6892	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4208	Discontinued
0.6884	Remote Similarity	NPD2979	Phase 3
0.6879	Remote Similarity	NPD6100	Approved
0.6879	Remote Similarity	NPD6099	Approved
0.6875	Remote Similarity	NPD8131	Suspended
0.6875	Remote Similarity	NPD7636	Approved
0.6871	Remote Similarity	NPD5699	Approved
0.687	Remote Similarity	NPD3143	Discontinued
0.6866	Remote Similarity	NPD4103	Phase 2
0.6866	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1791	Approved
0.685	Remote Similarity	NPD1793	Approved
0.6849	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1669	Approved
0.6822	Remote Similarity	NPD9615	Approved
0.6822	Remote Similarity	NPD9616	Approved
0.6822	Remote Similarity	NPD9613	Approved
0.6812	Remote Similarity	NPD6405	Approved
0.6812	Remote Similarity	NPD6407	Approved
0.6812	Remote Similarity	NPD8032	Phase 2
0.6809	Remote Similarity	NPD1753	Discontinued
0.6803	Remote Similarity	NPD6090	Discontinued
0.6797	Remote Similarity	NPD709	Approved
0.6794	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1778	Approved
0.6788	Remote Similarity	NPD7008	Discontinued
0.6786	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2157	Approved
0.6783	Remote Similarity	NPD4256	Phase 2
0.6783	Remote Similarity	NPD4257	Approved
0.6781	Remote Similarity	NPD2421	Approved
0.6781	Remote Similarity	NPD2420	Approved
0.6777	Remote Similarity	NPD9500	Approved
0.6774	Remote Similarity	NPD2684	Approved
0.6769	Remote Similarity	NPD316	Approved
0.6767	Remote Similarity	NPD3070	Discontinued
0.6763	Remote Similarity	NPD3109	Approved
0.6763	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3110	Approved
0.6763	Remote Similarity	NPD1613	Approved
0.675	Remote Similarity	NPD3028	Approved
0.6748	Remote Similarity	NPD968	Approved
0.6746	Remote Similarity	NPD228	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