NPASS Compound

Structure

CID72667 OpenBabel06191715412D 22 24 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 -1.3660 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 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 2.5981 -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 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 1.7321 -2.0000 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 0.0000 1.0000 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 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 14 2 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 11 18 2 0 0 0 0 12 13 1 0 0 0 0 13 16 2 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.19
Volume:	333.205
LogP:	4.963
LogD:	4.328
LogS:	-5.413
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.782
Synthetic Accessibility Score:	3.473
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.004
MDCK Permeability:	1.5221583453239873e-05
Pgp-inhibitor:	0.916
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	98.49134063720703%
Volume Distribution (VD):	1.197
Pgp-substrate:	3.1163954734802246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.808
CYP1A2-substrate:	0.88
CYP2C19-inhibitor:	0.845
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.584
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.791
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.696
CYP3A4-substrate:	0.706

ADMET: Excretion

Clearance (CL):	3.833
Half-life (T1/2):	0.153

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.243
Drug-inuced Liver Injury (DILI):	0.284
AMES Toxicity:	0.202
Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.247
Carcinogencity:	0.718
Eye Corrosion:	0.006
Eye Irritation:	0.868
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC72667

Natural Product ID:	NPC72667
*Common Name:**	5,6-Dehydrosugiol
IUPAC Name:	(4aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4-dihydro-2H-phenanthren-9-one
Synonyms:
Standard InCHIKey:	HUMGJQLBBAYPNM-HXUWFJFHSA-N
Standard InCHI:	InChI=1S/C20H26O2/c1-12(2)13-9-14-15(10-16(13)21)20(5)8-6-7-19(3,4)18(20)11-17(14)22/h9-12,21H,6-8H2,1-5H3/t20-/m1/s1
SMILES:	O=C1C=C2C(C)(C)CCC[C@@]2(c2c1cc(C(C)C)c(c2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3093123
PubChem CID:	14827280
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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	whole plants	east Texas, USA	2009-2011	PMID[24210499]
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24210499]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2267	Liatris tenuifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2267	Liatris tenuifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8215	Crepis zacintha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2267	Liatris tenuifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7646	Edgeworthia chrysantha	Species	Thymelaeaceae	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
GI50	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	92780.0	nM	PMID[515510]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	>	100000.0	nM	PMID[515510]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	84520.0	nM	PMID[515510]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	>	100000.0	nM	PMID[515510]

☑ 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 NPC72667 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	324
0.1-0.2	1584
0.2-0.3	3022
0.3-0.4	8140
0.4-0.5	10591
0.5-0.6	6955
0.6-0.7	8826
0.7-0.8	2800
0.8-0.85	327
0.85-0.9	93
0.9-0.95	19
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC254492
0.9836	High Similarity	NPC171460
0.9835	High Similarity	NPC78364
0.9835	High Similarity	NPC84672
0.9835	High Similarity	NPC176130
0.9835	High Similarity	NPC69424
0.975	High Similarity	NPC199273
0.9597	High Similarity	NPC108129
0.9593	High Similarity	NPC96024
0.9583	High Similarity	NPC282577
0.952	High Similarity	NPC471851
0.9516	High Similarity	NPC276238
0.9516	High Similarity	NPC303910
0.95	High Similarity	NPC154696
0.9435	High Similarity	NPC3009
0.937	High Similarity	NPC78307
0.937	High Similarity	NPC477139
0.937	High Similarity	NPC138472
0.935	High Similarity	NPC123506
0.9297	High Similarity	NPC202225
0.9256	High Similarity	NPC259703
0.9256	High Similarity	NPC32322
0.9219	High Similarity	NPC111845
0.9084	High Similarity	NPC36868
0.9084	High Similarity	NPC475957
0.9055	High Similarity	NPC117899
0.904	High Similarity	NPC137750
0.9032	High Similarity	NPC273683
0.9015	High Similarity	NPC230811
0.9008	High Similarity	NPC471670
0.8976	High Similarity	NPC193203
0.8968	High Similarity	NPC71610
0.8952	High Similarity	NPC176208
0.8939	High Similarity	NPC53001
0.8931	High Similarity	NPC153088
0.8915	High Similarity	NPC239134
0.8915	High Similarity	NPC18798
0.888	High Similarity	NPC471187
0.888	High Similarity	NPC275145
0.8872	High Similarity	NPC87723
0.8871	High Similarity	NPC162935
0.8871	High Similarity	NPC249340
0.8855	High Similarity	NPC12070
0.8855	High Similarity	NPC50924
0.8828	High Similarity	NPC229894
0.8819	High Similarity	NPC15837
0.881	High Similarity	NPC181334
0.88	High Similarity	NPC11250
0.8797	High Similarity	NPC277559
0.879	High Similarity	NPC241001
0.8788	High Similarity	NPC249272
0.8779	High Similarity	NPC114183
0.8769	High Similarity	NPC164295
0.8741	High Similarity	NPC471853
0.8722	High Similarity	NPC474311
0.872	High Similarity	NPC120545
0.8712	High Similarity	NPC270899
0.8702	High Similarity	NPC165612
0.8692	High Similarity	NPC253488
0.8686	High Similarity	NPC100242
0.8682	High Similarity	NPC48248
0.8657	High Similarity	NPC49911
0.8651	High Similarity	NPC91478
0.8651	High Similarity	NPC307174
0.8651	High Similarity	NPC121168
0.8647	High Similarity	NPC477596
0.8647	High Similarity	NPC283088
0.864	High Similarity	NPC190971
0.8636	High Similarity	NPC53896
0.8636	High Similarity	NPC4170
0.8636	High Similarity	NPC59459
0.8626	High Similarity	NPC17083
0.8626	High Similarity	NPC476847
0.8626	High Similarity	NPC244699
0.8626	High Similarity	NPC41847
0.8626	High Similarity	NPC93015
0.8615	High Similarity	NPC34414
0.8615	High Similarity	NPC146647
0.8615	High Similarity	NPC25736
0.8613	High Similarity	NPC308572
0.8613	High Similarity	NPC248068
0.8613	High Similarity	NPC477209
0.8607	High Similarity	NPC322197
0.8605	High Similarity	NPC471530
0.8605	High Similarity	NPC19432
0.8603	High Similarity	NPC169452
0.8603	High Similarity	NPC181560
0.8595	High Similarity	NPC242136
0.8583	High Similarity	NPC198014
0.8583	High Similarity	NPC174991
0.8582	High Similarity	NPC7464
0.8582	High Similarity	NPC472308
0.8582	High Similarity	NPC191976
0.8571	High Similarity	NPC477594
0.8571	High Similarity	NPC253627
0.8561	High Similarity	NPC478160
0.8561	High Similarity	NPC183103
0.8561	High Similarity	NPC58685
0.856	High Similarity	NPC190501
0.856	High Similarity	NPC318552
0.856	High Similarity	NPC478121
0.855	High Similarity	NPC27659
0.8529	High Similarity	NPC138099
0.8529	High Similarity	NPC242994
0.8527	High Similarity	NPC474737
0.8527	High Similarity	NPC3224
0.8527	High Similarity	NPC160499
0.8519	High Similarity	NPC471905
0.8516	High Similarity	NPC173978
0.8516	High Similarity	NPC142956
0.8516	High Similarity	NPC164014
0.8512	High Similarity	NPC231717
0.8512	High Similarity	NPC250323
0.8507	High Similarity	NPC80035
0.8507	High Similarity	NPC22644
0.8507	High Similarity	NPC290803
0.8496	Intermediate Similarity	NPC49742
0.8496	Intermediate Similarity	NPC267205
0.8496	Intermediate Similarity	NPC115458
0.8496	Intermediate Similarity	NPC225051
0.8496	Intermediate Similarity	NPC52407
0.8492	Intermediate Similarity	NPC472981
0.8489	Intermediate Similarity	NPC309169
0.8489	Intermediate Similarity	NPC196941
0.8485	Intermediate Similarity	NPC72669
0.8485	Intermediate Similarity	NPC291001
0.8485	Intermediate Similarity	NPC474517
0.848	Intermediate Similarity	NPC42657
0.8478	Intermediate Similarity	NPC193555
0.8478	Intermediate Similarity	NPC184935
0.8478	Intermediate Similarity	NPC201297
0.8473	Intermediate Similarity	NPC99731
0.8468	Intermediate Similarity	NPC174087
0.8467	Intermediate Similarity	NPC476534
0.8456	Intermediate Similarity	NPC51531
0.8456	Intermediate Similarity	NPC46242
0.8456	Intermediate Similarity	NPC157284
0.8456	Intermediate Similarity	NPC23667
0.8456	Intermediate Similarity	NPC13715
0.8456	Intermediate Similarity	NPC4214
0.8456	Intermediate Similarity	NPC473479
0.8456	Intermediate Similarity	NPC473779
0.8456	Intermediate Similarity	NPC165191
0.8456	Intermediate Similarity	NPC114333
0.8456	Intermediate Similarity	NPC289358
0.8456	Intermediate Similarity	NPC469857
0.8456	Intermediate Similarity	NPC42384
0.8456	Intermediate Similarity	NPC5014
0.8456	Intermediate Similarity	NPC297797
0.8456	Intermediate Similarity	NPC50615
0.8456	Intermediate Similarity	NPC28592
0.8456	Intermediate Similarity	NPC149773
0.8456	Intermediate Similarity	NPC477849
0.8456	Intermediate Similarity	NPC245760
0.8456	Intermediate Similarity	NPC91887
0.845	Intermediate Similarity	NPC87985
0.8444	Intermediate Similarity	NPC254847
0.844	Intermediate Similarity	NPC5568
0.8433	Intermediate Similarity	NPC282780
0.8433	Intermediate Similarity	NPC166480
0.843	Intermediate Similarity	NPC260323
0.843	Intermediate Similarity	NPC176279
0.8421	Intermediate Similarity	NPC312560
0.8421	Intermediate Similarity	NPC175738
0.8417	Intermediate Similarity	NPC478164
0.8413	Intermediate Similarity	NPC285829
0.8413	Intermediate Similarity	NPC206778
0.8409	Intermediate Similarity	NPC55949
0.8397	Intermediate Similarity	NPC282923
0.8394	Intermediate Similarity	NPC294330
0.8387	Intermediate Similarity	NPC471668
0.8387	Intermediate Similarity	NPC477453
0.8385	Intermediate Similarity	NPC306765
0.8382	Intermediate Similarity	NPC53206
0.8382	Intermediate Similarity	NPC477592
0.8382	Intermediate Similarity	NPC53414
0.8382	Intermediate Similarity	NPC119542
0.8372	Intermediate Similarity	NPC68756
0.8372	Intermediate Similarity	NPC152525
0.837	Intermediate Similarity	NPC258502
0.8369	Intermediate Similarity	NPC143685
0.8359	Intermediate Similarity	NPC300274
0.8358	Intermediate Similarity	NPC263817
0.8347	Intermediate Similarity	NPC13482
0.8346	Intermediate Similarity	NPC216216
0.8346	Intermediate Similarity	NPC85342
0.8345	Intermediate Similarity	NPC135524
0.8345	Intermediate Similarity	NPC19631
0.8345	Intermediate Similarity	NPC239136
0.8333	Intermediate Similarity	NPC131684
0.8333	Intermediate Similarity	NPC79933
0.8333	Intermediate Similarity	NPC31296
0.8333	Intermediate Similarity	NPC258366
0.8333	Intermediate Similarity	NPC473527
0.8333	Intermediate Similarity	NPC92624
0.8333	Intermediate Similarity	NPC473767
0.8333	Intermediate Similarity	NPC473974
0.8321	Intermediate Similarity	NPC471974
0.8321	Intermediate Similarity	NPC469680
0.8321	Intermediate Similarity	NPC61398

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 NPC72667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	966
0.2-0.3	1239
0.3-0.4	2582
0.4-0.5	2287
0.5-0.6	1200
0.6-0.7	457
0.7-0.8	84
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.871	High Similarity	NPD2932	Approved
0.8629	High Similarity	NPD4196	Clinical (unspecified phase)
0.856	High Similarity	NPD3019	Approved
0.8444	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8281	Intermediate Similarity	NPD1201	Approved
0.8168	Intermediate Similarity	NPD1470	Approved
0.8099	Intermediate Similarity	NPD7390	Discontinued
0.8095	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD7003	Approved
0.7986	Intermediate Similarity	NPD5404	Approved
0.7986	Intermediate Similarity	NPD5405	Approved
0.7986	Intermediate Similarity	NPD5406	Approved
0.7986	Intermediate Similarity	NPD5408	Approved
0.7937	Intermediate Similarity	NPD5951	Approved
0.7923	Intermediate Similarity	NPD3026	Approved
0.7923	Intermediate Similarity	NPD3023	Approved
0.7907	Intermediate Similarity	NPD3025	Approved
0.7907	Intermediate Similarity	NPD3024	Approved
0.7803	Intermediate Similarity	NPD3972	Approved
0.771	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD7458	Discontinued
0.7681	Intermediate Similarity	NPD6663	Approved
0.7671	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3300	Phase 2
0.7647	Intermediate Similarity	NPD5736	Approved
0.7639	Intermediate Similarity	NPD8166	Discontinued
0.7638	Intermediate Similarity	NPD7635	Approved
0.763	Intermediate Similarity	NPD1164	Approved
0.7606	Intermediate Similarity	NPD6099	Approved
0.7606	Intermediate Similarity	NPD6100	Approved
0.7576	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3091	Approved
0.7556	Intermediate Similarity	NPD1283	Approved
0.7552	Intermediate Similarity	NPD2346	Discontinued
0.752	Intermediate Similarity	NPD2342	Discontinued
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD1651	Approved
0.7483	Intermediate Similarity	NPD2935	Discontinued
0.746	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD2798	Approved
0.7444	Intermediate Similarity	NPD4626	Approved
0.7444	Intermediate Similarity	NPD4059	Approved
0.7417	Intermediate Similarity	NPD1809	Phase 2
0.7413	Intermediate Similarity	NPD2799	Discontinued
0.7402	Intermediate Similarity	NPD4750	Phase 3
0.7397	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1607	Approved
0.7383	Intermediate Similarity	NPD6273	Approved
0.7381	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD3020	Approved
0.7357	Intermediate Similarity	NPD3764	Approved
0.7355	Intermediate Similarity	NPD3495	Discontinued
0.7355	Intermediate Similarity	NPD288	Approved
0.7353	Intermediate Similarity	NPD1755	Approved
0.7351	Intermediate Similarity	NPD3226	Approved
0.7333	Intermediate Similarity	NPD1281	Approved
0.7333	Intermediate Similarity	NPD3092	Approved
0.7329	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2344	Approved
0.7299	Intermediate Similarity	NPD1876	Approved
0.7292	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4628	Phase 3
0.7279	Intermediate Similarity	NPD3750	Approved
0.7279	Intermediate Similarity	NPD4878	Approved
0.7273	Intermediate Similarity	NPD7819	Suspended
0.7273	Intermediate Similarity	NPD844	Approved
0.726	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1240	Approved
0.725	Intermediate Similarity	NPD7473	Discontinued
0.7237	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD7610	Discontinued
0.7215	Intermediate Similarity	NPD6959	Discontinued
0.7209	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2532	Approved
0.72	Intermediate Similarity	NPD2534	Approved
0.72	Intermediate Similarity	NPD1929	Approved
0.72	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1930	Approved
0.72	Intermediate Similarity	NPD2533	Approved
0.72	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3095	Discontinued
0.7183	Intermediate Similarity	NPD8032	Phase 2
0.7177	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1510	Phase 2
0.717	Intermediate Similarity	NPD6232	Discontinued
0.7164	Intermediate Similarity	NPD9545	Approved
0.7163	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7008	Discontinued
0.7154	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6651	Approved
0.7132	Intermediate Similarity	NPD3021	Approved
0.7132	Intermediate Similarity	NPD3022	Approved
0.7131	Intermediate Similarity	NPD2859	Approved
0.7131	Intermediate Similarity	NPD2860	Approved
0.7122	Intermediate Similarity	NPD3094	Phase 2
0.7114	Intermediate Similarity	NPD2309	Approved
0.7114	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5691	Approved
0.7107	Intermediate Similarity	NPD845	Approved
0.7101	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2066	Phase 3
0.7095	Intermediate Similarity	NPD2800	Approved
0.7086	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1751	Approved
0.7059	Intermediate Similarity	NPD2286	Discontinued
0.7054	Intermediate Similarity	NPD74	Approved
0.7054	Intermediate Similarity	NPD9266	Approved
0.7051	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2933	Approved
0.7049	Intermediate Similarity	NPD2934	Approved
0.7037	Intermediate Similarity	NPD7009	Phase 2
0.7034	Intermediate Similarity	NPD4097	Suspended
0.7021	Intermediate Similarity	NPD4208	Discontinued
0.7015	Intermediate Similarity	NPD9493	Approved
0.7014	Intermediate Similarity	NPD2979	Phase 3
0.7006	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2797	Approved
0.6993	Remote Similarity	NPD2313	Discontinued
0.6993	Remote Similarity	NPD3268	Approved
0.6985	Remote Similarity	NPD4093	Discontinued
0.6977	Remote Similarity	NPD9263	Approved
0.6977	Remote Similarity	NPD9267	Approved
0.6977	Remote Similarity	NPD9264	Approved
0.6968	Remote Similarity	NPD4380	Phase 2
0.6954	Remote Similarity	NPD7236	Approved
0.6951	Remote Similarity	NPD6020	Phase 2
0.6951	Remote Similarity	NPD5844	Phase 1
0.6939	Remote Similarity	NPD3748	Approved
0.6939	Remote Similarity	NPD4308	Phase 3
0.6913	Remote Similarity	NPD1549	Phase 2
0.6906	Remote Similarity	NPD9269	Phase 2
0.6906	Remote Similarity	NPD1608	Approved
0.6901	Remote Similarity	NPD3635	Approved
0.6901	Remote Similarity	NPD9494	Approved
0.6901	Remote Similarity	NPD3636	Approved
0.6901	Remote Similarity	NPD3637	Approved
0.6897	Remote Similarity	NPD4060	Phase 1
0.6894	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2796	Approved
0.6889	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4879	Approved
0.6875	Remote Similarity	NPD1237	Approved
0.6863	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD9268	Approved
0.6859	Remote Similarity	NPD6599	Discontinued
0.6859	Remote Similarity	NPD7028	Phase 2
0.6853	Remote Similarity	NPD2605	Approved
0.6853	Remote Similarity	NPD2606	Approved
0.6853	Remote Similarity	NPD4207	Discontinued
0.6846	Remote Similarity	NPD1471	Phase 3
0.6846	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7239	Suspended
0.6831	Remote Similarity	NPD2194	Approved
0.6831	Remote Similarity	NPD2195	Approved
0.6831	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4624	Approved
0.6824	Remote Similarity	NPD8150	Discontinued
0.6815	Remote Similarity	NPD7411	Suspended
0.6813	Remote Similarity	NPD7075	Discontinued
0.6812	Remote Similarity	NPD4589	Approved
0.6809	Remote Similarity	NPD6696	Suspended
0.6806	Remote Similarity	NPD5155	Approved
0.6806	Remote Similarity	NPD4625	Phase 3
0.6806	Remote Similarity	NPD5156	Approved
0.6797	Remote Similarity	NPD1511	Approved
0.6791	Remote Similarity	NPD1241	Discontinued
0.6791	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7177	Discontinued
0.6781	Remote Similarity	NPD4140	Approved
0.6781	Remote Similarity	NPD3620	Phase 2
0.6781	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2531	Phase 2
0.6779	Remote Similarity	NPD4477	Approved
0.6779	Remote Similarity	NPD4476	Approved
0.6779	Remote Similarity	NPD2438	Suspended
0.6772	Remote Similarity	NPD1934	Approved
0.6763	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7631	Approved
0.6744	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1792	Phase 2
0.6741	Remote Similarity	NPD2629	Approved
0.6741	Remote Similarity	NPD497	Approved
0.6738	Remote Similarity	NPD4749	Approved
0.6738	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3595	Approved
0.6736	Remote Similarity	NPD3594	Approved
0.6735	Remote Similarity	NPD230	Phase 1
0.673	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2801	Approved
0.6719	Remote Similarity	NPD940	Approved
0.6719	Remote Similarity	NPD1932	Approved
0.6719	Remote Similarity	NPD846	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