NPASS Compound

Structure

CID153088 OpenBabel06191715522D 22 24 0 0 0 0 0 0 0 0999 V2000 1.7321 -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 -4.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -0.8660 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 -2.5981 -1.5000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 0.8660 -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 -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 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 0.0000 0.0000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 19 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 12 1 0 0 0 0 11 15 1 0 0 0 0 12 17 2 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 20 2 0 0 0 0 15 16 1 0 0 0 0 15 18 2 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.16
Volume:	322.063
LogP:	4.659
LogD:	3.492
LogS:	-4.156
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	2.81
Fsp3:	0.421
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.82
MDCK Permeability:	1.7033922631526366e-05
Pgp-inhibitor:	0.909
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.695

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	99.14594268798828%
Volume Distribution (VD):	1.515
Pgp-substrate:	1.6507649421691895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.942
CYP1A2-substrate:	0.871
CYP2C19-inhibitor:	0.569
CYP2C19-substrate:	0.193
CYP2C9-inhibitor:	0.647
CYP2C9-substrate:	0.739
CYP2D6-inhibitor:	0.724
CYP2D6-substrate:	0.56
CYP3A4-inhibitor:	0.265
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	1.379
Half-life (T1/2):	0.199

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.767
AMES Toxicity:	0.468
Rat Oral Acute Toxicity:	0.279
Maximum Recommended Daily Dose:	0.723
Skin Sensitization:	0.925
Carcinogencity:	0.384
Eye Corrosion:	0.004
Eye Irritation:	0.913
Respiratory Toxicity:	0.681

Download Data

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

Natural Product: NPC153088

Natural Product ID:	NPC153088
*Common Name:**	Miltiodiol
IUPAC Name:	5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3-dihydrophenanthren-4-one
Synonyms:	Miltiodiol
Standard InCHIKey:	CEIJAQIIDANFLF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H22O3/c1-10(2)12-9-11-5-6-13-16(15(11)18(22)17(12)21)14(20)7-8-19(13,3)4/h5-6,9-10,21-22H,7-8H2,1-4H3
SMILES:	O=C1CCC(c2c1c1c(cc2)cc(c(c1O)O)C(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813350
PubChem CID:	11011966
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]
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]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	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]
NPO6095	Xanthoparmelia verruculifera	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28354	Tragacantha stipulosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28520	Heliotropium subulatum	Species	Heliotropiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	66300.0	nM	PMID[529867]

☑ 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 NPC153088 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	366
0.1-0.2	1609
0.2-0.3	3376
0.3-0.4	9227
0.4-0.5	10009
0.5-0.6	5518
0.6-0.7	9411
0.7-0.8	2881
0.8-0.85	227
0.85-0.9	64
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.969	High Similarity	NPC111845
0.9538	High Similarity	NPC138472
0.938	High Similarity	NPC276238
0.9191	High Similarity	NPC471853
0.9185	High Similarity	NPC230811
0.9111	High Similarity	NPC49911
0.9111	High Similarity	NPC277559
0.9104	High Similarity	NPC258502
0.9091	High Similarity	NPC291001
0.9077	High Similarity	NPC84672
0.9077	High Similarity	NPC69424
0.9077	High Similarity	NPC176130
0.9077	High Similarity	NPC78364
0.9058	High Similarity	NPC248068
0.9015	High Similarity	NPC108129
0.9008	High Similarity	NPC96024
0.8931	High Similarity	NPC72667
0.8929	High Similarity	NPC196941
0.8929	High Similarity	NPC309169
0.8905	High Similarity	NPC416
0.8905	High Similarity	NPC61398
0.8889	High Similarity	NPC293454
0.8864	High Similarity	NPC234175
0.8855	High Similarity	NPC254492
0.8846	High Similarity	NPC199273
0.8837	High Similarity	NPC176208
0.8815	High Similarity	NPC294226
0.8806	High Similarity	NPC471851
0.8797	High Similarity	NPC303910
0.8797	High Similarity	NPC171460
0.8786	High Similarity	NPC184935
0.8777	High Similarity	NPC476534
0.8768	High Similarity	NPC471974
0.8768	High Similarity	NPC469681
0.8768	High Similarity	NPC469680
0.8759	High Similarity	NPC7464
0.875	High Similarity	NPC202225
0.8741	High Similarity	NPC52692
0.8676	High Similarity	NPC78307
0.8676	High Similarity	NPC4170
0.8676	High Similarity	NPC477139
0.8633	High Similarity	NPC473779
0.8633	High Similarity	NPC46242
0.8633	High Similarity	NPC51531
0.8633	High Similarity	NPC297797
0.8633	High Similarity	NPC477849
0.8633	High Similarity	NPC157284
0.8633	High Similarity	NPC50615
0.8633	High Similarity	NPC165191
0.8633	High Similarity	NPC245760
0.8633	High Similarity	NPC28592
0.8633	High Similarity	NPC289358
0.8633	High Similarity	NPC469857
0.8633	High Similarity	NPC23667
0.8633	High Similarity	NPC473479
0.8633	High Similarity	NPC114333
0.8633	High Similarity	NPC149773
0.8633	High Similarity	NPC5014
0.8633	High Similarity	NPC42384
0.8633	High Similarity	NPC91887
0.8615	High Similarity	NPC154696
0.8601	High Similarity	NPC470038
0.8592	High Similarity	NPC199936
0.8582	High Similarity	NPC3009
0.8582	High Similarity	NPC48248
0.8571	High Similarity	NPC294330
0.8561	High Similarity	NPC264022
0.8561	High Similarity	NPC475957
0.8561	High Similarity	NPC15127
0.855	High Similarity	NPC282577
0.8538	High Similarity	NPC32322
0.8538	High Similarity	NPC259703
0.8521	High Similarity	NPC141817
0.8521	High Similarity	NPC192597
0.8521	High Similarity	NPC176030
0.8521	High Similarity	NPC229218
0.8521	High Similarity	NPC169214
0.8511	High Similarity	NPC473527
0.8511	High Similarity	NPC470035
0.85	High Similarity	NPC141368
0.85	High Similarity	NPC206207
0.8496	Intermediate Similarity	NPC137750
0.8483	Intermediate Similarity	NPC10842
0.8478	Intermediate Similarity	NPC50924
0.8473	Intermediate Similarity	NPC120545
0.8472	Intermediate Similarity	NPC75295
0.8472	Intermediate Similarity	NPC68441
0.8456	Intermediate Similarity	NPC117609
0.8451	Intermediate Similarity	NPC92079
0.8429	Intermediate Similarity	NPC147418
0.8429	Intermediate Similarity	NPC53001
0.8421	Intermediate Similarity	NPC181334
0.8421	Intermediate Similarity	NPC142956
0.8417	Intermediate Similarity	NPC283088
0.8409	Intermediate Similarity	NPC91478
0.8406	Intermediate Similarity	NPC225051
0.8406	Intermediate Similarity	NPC114183
0.8394	Intermediate Similarity	NPC474517
0.8394	Intermediate Similarity	NPC93015
0.8394	Intermediate Similarity	NPC72669
0.8394	Intermediate Similarity	NPC476847
0.8392	Intermediate Similarity	NPC30846
0.8392	Intermediate Similarity	NPC469855
0.8392	Intermediate Similarity	NPC471971
0.8392	Intermediate Similarity	NPC471972
0.838	Intermediate Similarity	NPC181560
0.838	Intermediate Similarity	NPC169452
0.838	Intermediate Similarity	NPC203063
0.8378	Intermediate Similarity	NPC306011
0.8378	Intermediate Similarity	NPC35
0.8378	Intermediate Similarity	NPC472838
0.8372	Intermediate Similarity	NPC16030
0.8369	Intermediate Similarity	NPC87723
0.8358	Intermediate Similarity	NPC123506
0.8346	Intermediate Similarity	NPC471187
0.8345	Intermediate Similarity	NPC270899
0.8345	Intermediate Similarity	NPC225351
0.8345	Intermediate Similarity	NPC258856
0.8345	Intermediate Similarity	NPC12070
0.8333	Intermediate Similarity	NPC249340
0.8333	Intermediate Similarity	NPC162935
0.8322	Intermediate Similarity	NPC164912
0.8311	Intermediate Similarity	NPC470037
0.831	Intermediate Similarity	NPC138099
0.831	Intermediate Similarity	NPC242994
0.8309	Intermediate Similarity	NPC229894
0.8298	Intermediate Similarity	NPC36868
0.8298	Intermediate Similarity	NPC290030
0.8296	Intermediate Similarity	NPC160499
0.8288	Intermediate Similarity	NPC143685
0.8288	Intermediate Similarity	NPC39361
0.8286	Intermediate Similarity	NPC80035
0.8286	Intermediate Similarity	NPC249272
0.8284	Intermediate Similarity	NPC173978
0.8278	Intermediate Similarity	NPC213401
0.8276	Intermediate Similarity	NPC8493
0.8276	Intermediate Similarity	NPC126707
0.8276	Intermediate Similarity	NPC294679
0.8276	Intermediate Similarity	NPC469854
0.8276	Intermediate Similarity	NPC145301
0.8276	Intermediate Similarity	NPC469856
0.8276	Intermediate Similarity	NPC469375
0.8276	Intermediate Similarity	NPC144247
0.8273	Intermediate Similarity	NPC115458
0.8273	Intermediate Similarity	NPC52407
0.8271	Intermediate Similarity	NPC11250
0.8264	Intermediate Similarity	NPC239136
0.8264	Intermediate Similarity	NPC19631
0.8264	Intermediate Similarity	NPC11314
0.8264	Intermediate Similarity	NPC193555
0.8261	Intermediate Similarity	NPC18798
0.8261	Intermediate Similarity	NPC41847
0.8261	Intermediate Similarity	NPC243305
0.8261	Intermediate Similarity	NPC244699
0.8258	Intermediate Similarity	NPC190971
0.8258	Intermediate Similarity	NPC241001
0.8255	Intermediate Similarity	NPC144283
0.8255	Intermediate Similarity	NPC302783
0.8255	Intermediate Similarity	NPC473201
0.8255	Intermediate Similarity	NPC118427
0.8248	Intermediate Similarity	NPC117899
0.8248	Intermediate Similarity	NPC99731
0.8243	Intermediate Similarity	NPC472837
0.8243	Intermediate Similarity	NPC142654
0.8239	Intermediate Similarity	NPC13715
0.8239	Intermediate Similarity	NPC4214
0.8235	Intermediate Similarity	NPC19432
0.8231	Intermediate Similarity	NPC150919
0.8231	Intermediate Similarity	NPC58373
0.8227	Intermediate Similarity	NPC155211
0.8227	Intermediate Similarity	NPC191976
0.8227	Intermediate Similarity	NPC194764
0.8227	Intermediate Similarity	NPC65005
0.8227	Intermediate Similarity	NPC264112
0.8227	Intermediate Similarity	NPC472308
0.8222	Intermediate Similarity	NPC87985
0.8219	Intermediate Similarity	NPC478160
0.8219	Intermediate Similarity	NPC73416
0.8219	Intermediate Similarity	NPC160777
0.8209	Intermediate Similarity	NPC275145
0.8209	Intermediate Similarity	NPC198014
0.8209	Intermediate Similarity	NPC273683
0.8207	Intermediate Similarity	NPC238629
0.8203	Intermediate Similarity	NPC317869
0.8201	Intermediate Similarity	NPC58685
0.8195	Intermediate Similarity	NPC253627
0.8188	Intermediate Similarity	NPC58310
0.8188	Intermediate Similarity	NPC295977
0.8188	Intermediate Similarity	NPC55949
0.8182	Intermediate Similarity	NPC472903
0.8182	Intermediate Similarity	NPC318552
0.8182	Intermediate Similarity	NPC190501
0.8175	Intermediate Similarity	NPC193203
0.8175	Intermediate Similarity	NPC282923
0.8169	Intermediate Similarity	NPC53414
0.8169	Intermediate Similarity	NPC471905
0.8169	Intermediate Similarity	NPC53206
0.8163	Intermediate Similarity	NPC471970
0.8163	Intermediate Similarity	NPC246229
0.8163	Intermediate Similarity	NPC273798

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 NPC153088 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	949
0.2-0.3	1347
0.3-0.4	2738
0.4-0.5	2142
0.5-0.6	1126
0.6-0.7	442
0.7-0.8	52
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8472	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3019	Approved
0.8099	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD1201	Approved
0.8045	Intermediate Similarity	NPD2932	Approved
0.797	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD1470	Approved
0.7943	Intermediate Similarity	NPD943	Approved
0.7917	Intermediate Similarity	NPD5408	Approved
0.7917	Intermediate Similarity	NPD5405	Approved
0.7917	Intermediate Similarity	NPD5404	Approved
0.7917	Intermediate Similarity	NPD5406	Approved
0.7905	Intermediate Similarity	NPD7390	Discontinued
0.7823	Intermediate Similarity	NPD7003	Approved
0.7823	Intermediate Similarity	NPD8166	Discontinued
0.775	Intermediate Similarity	NPD7473	Discontinued
0.7727	Intermediate Similarity	NPD5951	Approved
0.7673	Intermediate Similarity	NPD6232	Discontinued
0.7615	Intermediate Similarity	NPD3021	Approved
0.7615	Intermediate Similarity	NPD3022	Approved
0.7603	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2342	Discontinued
0.7591	Intermediate Similarity	NPD3023	Approved
0.7591	Intermediate Similarity	NPD3026	Approved
0.7576	Intermediate Similarity	NPD7635	Approved
0.7574	Intermediate Similarity	NPD3024	Approved
0.7574	Intermediate Similarity	NPD3025	Approved
0.7532	Intermediate Similarity	NPD7458	Discontinued
0.7483	Intermediate Similarity	NPD3300	Phase 2
0.7481	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2346	Discontinued
0.7379	Intermediate Similarity	NPD6663	Approved
0.7376	Intermediate Similarity	NPD1283	Approved
0.7365	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD3972	Approved
0.7343	Intermediate Similarity	NPD5736	Approved
0.7324	Intermediate Similarity	NPD1164	Approved
0.7319	Intermediate Similarity	NPD1651	Approved
0.7286	Intermediate Similarity	NPD3092	Approved
0.7266	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3091	Approved
0.7233	Intermediate Similarity	NPD2801	Approved
0.7229	Intermediate Similarity	NPD5844	Phase 1
0.7222	Intermediate Similarity	NPD9494	Approved
0.7209	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1511	Approved
0.7197	Intermediate Similarity	NPD3226	Approved
0.7192	Intermediate Similarity	NPD3764	Approved
0.717	Intermediate Similarity	NPD1934	Approved
0.7163	Intermediate Similarity	NPD1281	Approved
0.7152	Intermediate Similarity	NPD2344	Approved
0.7143	Intermediate Similarity	NPD4059	Approved
0.7133	Intermediate Similarity	NPD2799	Discontinued
0.7124	Intermediate Similarity	NPD4628	Phase 3
0.7123	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7008	Discontinued
0.7115	Intermediate Similarity	NPD1512	Approved
0.7115	Intermediate Similarity	NPD6273	Approved
0.7113	Intermediate Similarity	NPD4878	Approved
0.7113	Intermediate Similarity	NPD9269	Phase 2
0.7095	Intermediate Similarity	NPD3620	Phase 2
0.7095	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6099	Approved
0.7086	Intermediate Similarity	NPD2935	Discontinued
0.7086	Intermediate Similarity	NPD6100	Approved
0.7083	Intermediate Similarity	NPD3094	Phase 2
0.7073	Intermediate Similarity	NPD6959	Discontinued
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD3020	Approved
0.7037	Intermediate Similarity	NPD3882	Suspended
0.7037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2798	Approved
0.7021	Intermediate Similarity	NPD2286	Discontinued
0.7021	Intermediate Similarity	NPD4626	Approved
0.7019	Intermediate Similarity	NPD1465	Phase 2
0.7	Intermediate Similarity	NPD1607	Approved
0.6968	Remote Similarity	NPD6190	Approved
0.6968	Remote Similarity	NPD2309	Approved
0.6953	Remote Similarity	NPD1809	Phase 2
0.6946	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6166	Phase 2
0.6946	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1755	Approved
0.6943	Remote Similarity	NPD2532	Approved
0.6943	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2533	Approved
0.6943	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2534	Approved
0.6933	Remote Similarity	NPD230	Phase 1
0.6929	Remote Similarity	NPD7610	Discontinued
0.6919	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7819	Suspended
0.6913	Remote Similarity	NPD8032	Phase 2
0.6912	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3095	Discontinued
0.6899	Remote Similarity	NPD288	Approved
0.6897	Remote Similarity	NPD8150	Discontinued
0.6897	Remote Similarity	NPD1876	Approved
0.6894	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1930	Approved
0.6894	Remote Similarity	NPD1929	Approved
0.6889	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2420	Approved
0.6879	Remote Similarity	NPD2421	Approved
0.6879	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2979	Phase 3
0.6867	Remote Similarity	NPD1240	Approved
0.6867	Remote Similarity	NPD4060	Phase 1
0.6859	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6234	Discontinued
0.6846	Remote Similarity	NPD2313	Discontinued
0.6839	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7028	Phase 2
0.6832	Remote Similarity	NPD4380	Phase 2
0.6831	Remote Similarity	NPD9268	Approved
0.6831	Remote Similarity	NPD4093	Discontinued
0.6828	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD2859	Approved
0.6822	Remote Similarity	NPD844	Approved
0.6822	Remote Similarity	NPD2860	Approved
0.6818	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5494	Approved
0.6797	Remote Similarity	NPD845	Approved
0.6797	Remote Similarity	NPD1510	Phase 2
0.6795	Remote Similarity	NPD3750	Approved
0.6776	Remote Similarity	NPD4097	Suspended
0.6774	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD3495	Discontinued
0.6768	Remote Similarity	NPD5978	Approved
0.6768	Remote Similarity	NPD5977	Approved
0.6768	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3818	Discontinued
0.6753	Remote Similarity	NPD2438	Suspended
0.6748	Remote Similarity	NPD37	Approved
0.6744	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2934	Approved
0.6744	Remote Similarity	NPD2933	Approved
0.6742	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD2797	Approved
0.6733	Remote Similarity	NPD3268	Approved
0.6731	Remote Similarity	NPD2800	Approved
0.6728	Remote Similarity	NPD6599	Discontinued
0.6715	Remote Similarity	NPD4750	Phase 3
0.6714	Remote Similarity	NPD2629	Approved
0.6713	Remote Similarity	NPD5691	Approved
0.6692	Remote Similarity	NPD1932	Approved
0.6689	Remote Similarity	NPD258	Approved
0.6689	Remote Similarity	NPD257	Approved
0.6688	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7075	Discontinued
0.6687	Remote Similarity	NPD3749	Approved
0.6686	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD4625	Phase 3
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD5156	Approved
0.6667	Remote Similarity	NPD1751	Approved
0.6667	Remote Similarity	NPD5155	Approved
0.6667	Remote Similarity	NPD6651	Approved
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD3455	Phase 2
0.6667	Remote Similarity	NPD2066	Phase 3
0.6648	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2531	Phase 2
0.6644	Remote Similarity	NPD1608	Approved
0.6644	Remote Similarity	NPD4208	Discontinued
0.6643	Remote Similarity	NPD9545	Approved
0.6642	Remote Similarity	NPD2329	Discontinued
0.6629	Remote Similarity	NPD8312	Approved
0.6629	Remote Similarity	NPD8313	Approved
0.6628	Remote Similarity	NPD7054	Approved
0.6628	Remote Similarity	NPD6020	Phase 2
0.6627	Remote Similarity	NPD4967	Phase 2
0.6627	Remote Similarity	NPD4965	Approved
0.6627	Remote Similarity	NPD4966	Approved
0.6625	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD4879	Approved
0.6609	Remote Similarity	NPD5027	Approved
0.6609	Remote Similarity	NPD5029	Approved
0.6609	Remote Similarity	NPD5031	Approved
0.6606	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7236	Approved
0.6603	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD1471	Phase 3
0.6603	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2606	Approved
0.66	Remote Similarity	NPD2605	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