NPASS Compound

Structure

CID134882 OpenBabel06191715492D 21 23 0 0 0 0 0 0 0 0999 V2000 -2.5981 2.5000 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 3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -2.5981 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 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 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 -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 -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 -0.8660 -1.5000 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 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 18 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	282.16
Volume:	313.273
LogP:	6.201
LogD:	4.214
LogS:	-3.732
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	2.921
Fsp3:	0.368
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:	-4.876
MDCK Permeability:	1.4902848306519445e-05
Pgp-inhibitor:	0.918
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.938
30% Bioavailability (F30%):	0.739

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	98.63973236083984%
Volume Distribution (VD):	1.801
Pgp-substrate:	1.5421082973480225%

ADMET: Metabolism

CYP1A2-inhibitor:	0.954
CYP1A2-substrate:	0.834
CYP2C19-inhibitor:	0.696
CYP2C19-substrate:	0.116
CYP2C9-inhibitor:	0.529
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.711
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.245
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	3.232
Half-life (T1/2):	0.123

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.146
AMES Toxicity:	0.626
Rat Oral Acute Toxicity:	0.396
Maximum Recommended Daily Dose:	0.813
Skin Sensitization:	0.951
Carcinogencity:	0.163
Eye Corrosion:	0.009
Eye Irritation:	0.936
Respiratory Toxicity:	0.873

Download Data

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

Natural Product: NPC134882

Natural Product ID:	NPC134882
*Common Name:**	Sibiriquinone B
IUPAC Name:	8,8-dimethyl-2-propan-2-yl-6,7-dihydro-5H-phenanthrene-1,4-dione
Synonyms:	sibiriquinone b
Standard InCHIKey:	MRPWFJPXXDIFAE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H22O2/c1-11(2)14-10-16(20)17-12-6-5-9-19(3,4)15(12)8-7-13(17)18(14)21/h7-8,10-11H,5-6,9H2,1-4H3
SMILES:	CC(C1=CC(=O)c2c(C1=O)ccc1c2CCCC1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227074
PubChem CID:	9971020
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]
NPO11138	Veronicastrum sibiricum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11138	Veronicastrum sibiricum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11138	Veronicastrum sibiricum	Species	Plantaginaceae	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]
NPO11138	Veronicastrum sibiricum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	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	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
PROTEIN FAMILY	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	50000.0	nM	PMID[470709]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	3360.0	nM	PMID[470709]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	3180.0	nM	PMID[470709]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[470709]

☑ 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 NPC134882 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	326
0.1-0.2	1603
0.2-0.3	4183
0.3-0.4	14259
0.4-0.5	14921
0.5-0.6	6214
0.6-0.7	936
0.7-0.8	175
0.8-0.85	41
0.85-0.9	14
0.9-0.95	12
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC239185
0.989	High Similarity	NPC265220
0.9785	High Similarity	NPC109514
0.9785	High Similarity	NPC476993
0.9783	High Similarity	NPC75724
0.957	High Similarity	NPC49994
0.9565	High Similarity	NPC219573
0.9565	High Similarity	NPC185208
0.956	High Similarity	NPC238219
0.9457	High Similarity	NPC260233
0.9451	High Similarity	NPC59677
0.9451	High Similarity	NPC323420
0.9451	High Similarity	NPC155232
0.9451	High Similarity	NPC153885
0.9341	High Similarity	NPC133461
0.9239	High Similarity	NPC1682
0.9239	High Similarity	NPC188844
0.9231	High Similarity	NPC173413
0.914	High Similarity	NPC289883
0.913	High Similarity	NPC284475
0.91	High Similarity	NPC470252
0.9011	High Similarity	NPC157778
0.8913	High Similarity	NPC298115
0.8901	High Similarity	NPC43945
0.8817	High Similarity	NPC19256
0.8817	High Similarity	NPC277277
0.8791	High Similarity	NPC307
0.8791	High Similarity	NPC160339
0.875	High Similarity	NPC470253
0.871	High Similarity	NPC418308
0.8696	High Similarity	NPC69057
0.8667	High Similarity	NPC326664
0.8646	High Similarity	NPC472880
0.8602	High Similarity	NPC267262
0.86	High Similarity	NPC471829
0.86	High Similarity	NPC247976
0.86	High Similarity	NPC475939
0.86	High Similarity	NPC474866
0.86	High Similarity	NPC472691
0.8571	High Similarity	NPC143768
0.8558	High Similarity	NPC265513
0.8476	Intermediate Similarity	NPC280789
0.8462	Intermediate Similarity	NPC215008
0.84	Intermediate Similarity	NPC472879
0.8396	Intermediate Similarity	NPC93287
0.835	Intermediate Similarity	NPC472699
0.835	Intermediate Similarity	NPC472700
0.835	Intermediate Similarity	NPC100767
0.8333	Intermediate Similarity	NPC125226
0.8333	Intermediate Similarity	NPC329282
0.8318	Intermediate Similarity	NPC471721
0.8269	Intermediate Similarity	NPC472696
0.8269	Intermediate Similarity	NPC472695
0.8269	Intermediate Similarity	NPC472701
0.8269	Intermediate Similarity	NPC472683
0.8242	Intermediate Similarity	NPC145053
0.8241	Intermediate Similarity	NPC215419
0.8211	Intermediate Similarity	NPC153308
0.8182	Intermediate Similarity	NPC323440
0.8182	Intermediate Similarity	NPC80605
0.8182	Intermediate Similarity	NPC222968
0.8144	Intermediate Similarity	NPC103346
0.8132	Intermediate Similarity	NPC285716
0.8132	Intermediate Similarity	NPC190567
0.8132	Intermediate Similarity	NPC17408
0.8131	Intermediate Similarity	NPC218855
0.8131	Intermediate Similarity	NPC292834
0.8091	Intermediate Similarity	NPC469843
0.8077	Intermediate Similarity	NPC172483
0.8077	Intermediate Similarity	NPC474910
0.8065	Intermediate Similarity	NPC273758
0.8056	Intermediate Similarity	NPC471481
0.8043	Intermediate Similarity	NPC12936
0.8043	Intermediate Similarity	NPC273033
0.8036	Intermediate Similarity	NPC202015
0.8022	Intermediate Similarity	NPC300205
0.8	Intermediate Similarity	NPC164526
0.7982	Intermediate Similarity	NPC130591
0.7982	Intermediate Similarity	NPC234637
0.7946	Intermediate Similarity	NPC318173
0.7941	Intermediate Similarity	NPC221825
0.7938	Intermediate Similarity	NPC113307
0.7938	Intermediate Similarity	NPC325709
0.7935	Intermediate Similarity	NPC71664
0.7935	Intermediate Similarity	NPC164086
0.7921	Intermediate Similarity	NPC226041
0.7912	Intermediate Similarity	NPC285470
0.7912	Intermediate Similarity	NPC103488
0.7912	Intermediate Similarity	NPC2785
0.7912	Intermediate Similarity	NPC36342
0.7905	Intermediate Similarity	NPC471186
0.7895	Intermediate Similarity	NPC252067
0.7885	Intermediate Similarity	NPC274443
0.787	Intermediate Similarity	NPC474057
0.787	Intermediate Similarity	NPC137315
0.7864	Intermediate Similarity	NPC225079
0.7864	Intermediate Similarity	NPC133809
0.7864	Intermediate Similarity	NPC128248
0.7864	Intermediate Similarity	NPC136810
0.7857	Intermediate Similarity	NPC58872
0.7845	Intermediate Similarity	NPC328107
0.7838	Intermediate Similarity	NPC260886
0.7826	Intermediate Similarity	NPC151405
0.7826	Intermediate Similarity	NPC139901
0.7818	Intermediate Similarity	NPC67377
0.7802	Intermediate Similarity	NPC245966
0.7798	Intermediate Similarity	NPC186128
0.7788	Intermediate Similarity	NPC244427
0.7788	Intermediate Similarity	NPC222390
0.7757	Intermediate Similarity	NPC203732
0.7748	Intermediate Similarity	NPC217111
0.7748	Intermediate Similarity	NPC474095
0.7748	Intermediate Similarity	NPC93181
0.7745	Intermediate Similarity	NPC240042
0.7739	Intermediate Similarity	NPC472981
0.7736	Intermediate Similarity	NPC134120
0.7719	Intermediate Similarity	NPC476645
0.7714	Intermediate Similarity	NPC329556
0.7699	Intermediate Similarity	NPC268930
0.7699	Intermediate Similarity	NPC61651
0.7685	Intermediate Similarity	NPC192577
0.7684	Intermediate Similarity	NPC39600
0.7684	Intermediate Similarity	NPC197581
0.7677	Intermediate Similarity	NPC26224
0.7677	Intermediate Similarity	NPC303967
0.7677	Intermediate Similarity	NPC67585
0.7677	Intermediate Similarity	NPC110420
0.7672	Intermediate Similarity	NPC167323
0.7672	Intermediate Similarity	NPC269923
0.7652	Intermediate Similarity	NPC232958
0.7652	Intermediate Similarity	NPC238861
0.7652	Intermediate Similarity	NPC77000
0.7634	Intermediate Similarity	NPC272260
0.7609	Intermediate Similarity	NPC3190
0.7609	Intermediate Similarity	NPC9796
0.7609	Intermediate Similarity	NPC249018
0.76	Intermediate Similarity	NPC475023
0.76	Intermediate Similarity	NPC475059
0.7593	Intermediate Similarity	NPC112903
0.7593	Intermediate Similarity	NPC470007
0.7589	Intermediate Similarity	NPC228936
0.7579	Intermediate Similarity	NPC230068
0.7553	Intermediate Similarity	NPC95868
0.7553	Intermediate Similarity	NPC477703
0.7542	Intermediate Similarity	NPC85511
0.7542	Intermediate Similarity	NPC51079
0.7542	Intermediate Similarity	NPC318067
0.7525	Intermediate Similarity	NPC475057
0.7524	Intermediate Similarity	NPC112552
0.75	Intermediate Similarity	NPC185763
0.75	Intermediate Similarity	NPC142326
0.75	Intermediate Similarity	NPC94751
0.75	Intermediate Similarity	NPC83409
0.75	Intermediate Similarity	NPC37914
0.75	Intermediate Similarity	NPC476225
0.75	Intermediate Similarity	NPC241851
0.75	Intermediate Similarity	NPC196673
0.7478	Intermediate Similarity	NPC472698
0.7478	Intermediate Similarity	NPC472697
0.7477	Intermediate Similarity	NPC471189
0.7477	Intermediate Similarity	NPC471188
0.7477	Intermediate Similarity	NPC66208
0.7474	Intermediate Similarity	NPC100039
0.7474	Intermediate Similarity	NPC73978
0.7447	Intermediate Similarity	NPC159661
0.7438	Intermediate Similarity	NPC115797
0.7438	Intermediate Similarity	NPC478162
0.7438	Intermediate Similarity	NPC478165
0.7438	Intermediate Similarity	NPC51448
0.7436	Intermediate Similarity	NPC144547
0.7434	Intermediate Similarity	NPC186933
0.7419	Intermediate Similarity	NPC179726
0.7414	Intermediate Similarity	NPC204784
0.7411	Intermediate Similarity	NPC13784
0.7404	Intermediate Similarity	NPC156021
0.7387	Intermediate Similarity	NPC475002
0.7387	Intermediate Similarity	NPC95126
0.7387	Intermediate Similarity	NPC291799
0.7368	Intermediate Similarity	NPC135730
0.7368	Intermediate Similarity	NPC157055
0.7363	Intermediate Similarity	NPC54269
0.7363	Intermediate Similarity	NPC285679
0.7355	Intermediate Similarity	NPC474106
0.735	Intermediate Similarity	NPC472679
0.735	Intermediate Similarity	NPC289432
0.735	Intermediate Similarity	NPC988
0.735	Intermediate Similarity	NPC472680
0.7347	Intermediate Similarity	NPC123476
0.7345	Intermediate Similarity	NPC294458
0.7345	Intermediate Similarity	NPC196075
0.7333	Intermediate Similarity	NPC145052
0.7333	Intermediate Similarity	NPC295664
0.7308	Intermediate Similarity	NPC12695
0.7304	Intermediate Similarity	NPC158157
0.7295	Intermediate Similarity	NPC72667
0.7288	Intermediate Similarity	NPC476234
0.7264	Intermediate Similarity	NPC54647
0.7264	Intermediate Similarity	NPC476042
0.7253	Intermediate Similarity	NPC74458
0.725	Intermediate Similarity	NPC325740

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 NPC134882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	1023
0.2-0.3	1542
0.3-0.4	3303
0.4-0.5	2151
0.5-0.6	671
0.6-0.7	118
0.7-0.8	32
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.989	High Similarity	NPD3495	Discontinued
0.9239	High Similarity	NPD7631	Approved
0.913	High Similarity	NPD7609	Phase 3
0.8901	High Similarity	NPD650	Approved
0.8247	Intermediate Similarity	NPD1508	Approved
0.8043	Intermediate Similarity	NPD942	Approved
0.8037	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1843	Approved
0.7788	Intermediate Similarity	NPD7009	Phase 2
0.7767	Intermediate Similarity	NPD2066	Phase 3
0.7748	Intermediate Similarity	NPD5951	Approved
0.7714	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1929	Approved
0.7714	Intermediate Similarity	NPD1930	Approved
0.7699	Intermediate Similarity	NPD7610	Discontinued
0.7652	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1932	Approved
0.7586	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD6049	Phase 2
0.7549	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD2329	Discontinued
0.75	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2648	Phase 3
0.7453	Intermediate Similarity	NPD2193	Phase 2
0.7451	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD6858	Approved
0.7411	Intermediate Similarity	NPD7094	Approved
0.7364	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD5836	Discontinued
0.729	Intermediate Similarity	NPD2196	Discontinued
0.7288	Intermediate Similarity	NPD4879	Approved
0.7212	Intermediate Similarity	NPD4094	Approved
0.72	Intermediate Similarity	NPD1087	Approved
0.72	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD1088	Approved
0.7168	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4657	Approved
0.7075	Intermediate Similarity	NPD4655	Approved
0.7049	Intermediate Similarity	NPD6330	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1693	Approved
0.7	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD1317	Discontinued
0.699	Remote Similarity	NPD1089	Approved
0.699	Remote Similarity	NPD1090	Approved
0.699	Remote Similarity	NPD1086	Approved
0.6981	Remote Similarity	NPD1989	Approved
0.6972	Remote Similarity	NPD2171	Approved
0.6972	Remote Similarity	NPD6024	Approved
0.6972	Remote Similarity	NPD6027	Approved
0.697	Remote Similarity	NPD3971	Phase 1
0.6952	Remote Similarity	NPD1563	Approved
0.6937	Remote Similarity	NPD1677	Discontinued
0.6937	Remote Similarity	NPD2192	Approved
0.6937	Remote Similarity	NPD2197	Approved
0.6929	Remote Similarity	NPD7961	Discontinued
0.6923	Remote Similarity	NPD3317	Approved
0.6915	Remote Similarity	NPD4058	Approved
0.6905	Remote Similarity	NPD2754	Discontinued
0.6905	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7008	Discontinued
0.6893	Remote Similarity	NPD800	Approved
0.6887	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4878	Approved
0.6847	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5909	Discontinued
0.6783	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD2932	Approved
0.6762	Remote Similarity	NPD1239	Approved
0.6759	Remote Similarity	NPD1565	Approved
0.6759	Remote Similarity	NPD1099	Approved
0.6759	Remote Similarity	NPD1566	Phase 3
0.6759	Remote Similarity	NPD1100	Approved
0.6759	Remote Similarity	NPD1564	Approved
0.6757	Remote Similarity	NPD3357	Discontinued
0.6754	Remote Similarity	NPD2182	Approved
0.6752	Remote Similarity	NPD7076	Approved
0.6752	Remote Similarity	NPD7077	Approved
0.6748	Remote Similarity	NPD3972	Approved
0.6696	Remote Similarity	NPD1237	Approved
0.6696	Remote Similarity	NPD164	Approved
0.6696	Remote Similarity	NPD664	Approved
0.6694	Remote Similarity	NPD3025	Approved
0.6694	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD6287	Discontinued
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD3672	Approved
0.6639	Remote Similarity	NPD2345	Approved
0.6639	Remote Similarity	NPD3019	Approved
0.6636	Remote Similarity	NPD1202	Approved
0.6614	Remote Similarity	NPD7084	Phase 3
0.6596	Remote Similarity	NPD4691	Approved
0.6585	Remote Similarity	NPD3026	Approved
0.6585	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3023	Approved
0.6571	Remote Similarity	NPD5347	Phase 2
0.6571	Remote Similarity	NPD5346	Phase 2
0.6569	Remote Similarity	NPD4544	Approved
0.6562	Remote Similarity	NPD4687	Approved
0.6557	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD2508	Discontinued
0.6518	Remote Similarity	NPD813	Approved
0.6508	Remote Similarity	NPD1876	Approved
0.6504	Remote Similarity	NPD4199	Phase 3
0.6489	Remote Similarity	NPD4137	Phase 3
0.6471	Remote Similarity	NPD6010	Discontinued
0.6465	Remote Similarity	NPD227	Approved
0.6465	Remote Similarity	NPD225	Approved
0.6457	Remote Similarity	NPD1470	Approved
0.6457	Remote Similarity	NPD3245	Phase 3
0.6457	Remote Similarity	NPD3244	Pre-registration
0.6442	Remote Similarity	NPD9257	Approved
0.6442	Remote Similarity	NPD9259	Approved
0.6434	Remote Similarity	NPD7055	Discontinued
0.6429	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3549	Approved
0.6429	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3547	Approved
0.6423	Remote Similarity	NPD7003	Approved
0.6421	Remote Similarity	NPD4747	Approved
0.6412	Remote Similarity	NPD7713	Phase 3
0.6412	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1201	Approved
0.64	Remote Similarity	NPD9490	Approved
0.6392	Remote Similarity	NPD5733	Approved
0.6381	Remote Similarity	NPD4793	Discontinued
0.6372	Remote Similarity	NPD4803	Discontinued
0.6364	Remote Similarity	NPD3093	Approved
0.6354	Remote Similarity	NPD5276	Approved
0.6339	Remote Similarity	NPD1238	Approved
0.6339	Remote Similarity	NPD742	Approved
0.6336	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6647	Phase 2
0.6311	Remote Similarity	NPD9491	Approved
0.6311	Remote Similarity	NPD405	Clinical (unspecified phase)
0.629	Remote Similarity	NPD1245	Approved
0.629	Remote Similarity	NPD1651	Approved
0.6283	Remote Similarity	NPD6354	Discontinued
0.6281	Remote Similarity	NPD2629	Approved
0.6281	Remote Similarity	NPD2319	Discontinued
0.6279	Remote Similarity	NPD4980	Approved
0.6279	Remote Similarity	NPD2798	Approved
0.6275	Remote Similarity	NPD226	Approved
0.6271	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6065	Approved
0.626	Remote Similarity	NPD997	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.625	Remote Similarity	NPD466	Approved
0.6214	Remote Similarity	NPD7236	Approved
0.6204	Remote Similarity	NPD9258	Approved
0.6204	Remote Similarity	NPD9256	Approved
0.6204	Remote Similarity	NPD2346	Discontinued
0.6202	Remote Similarity	NPD5653	Discontinued
0.6195	Remote Similarity	NPD7798	Approved
0.6182	Remote Similarity	NPD2878	Approved
0.6182	Remote Similarity	NPD3982	Approved
0.6182	Remote Similarity	NPD3980	Approved
0.6176	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD5159	Phase 2
0.6172	Remote Similarity	NPD5157	Phase 1
0.6162	Remote Similarity	NPD9716	Approved
0.6161	Remote Similarity	NPD5597	Approved
0.6161	Remote Similarity	NPD5598	Approved
0.6154	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD4766	Approved
0.6148	Remote Similarity	NPD3867	Phase 2
0.6148	Remote Similarity	NPD1246	Approved
0.6142	Remote Similarity	NPD1281	Approved
0.6136	Remote Similarity	NPD6966	Discovery
0.6132	Remote Similarity	NPD3099	Discontinued
0.6131	Remote Similarity	NPD5408	Approved
0.6131	Remote Similarity	NPD5405	Approved
0.6131	Remote Similarity	NPD5406	Approved
0.6131	Remote Similarity	NPD5404	Approved
0.6129	Remote Similarity	NPD675	Discontinued
0.6129	Remote Similarity	NPD5991	Approved
0.6129	Remote Similarity	NPD5990	Approved
0.6124	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD2056	Discontinued
0.6116	Remote Similarity	NPD2607	Approved
0.6111	Remote Similarity	NPD7239	Suspended
0.6106	Remote Similarity	NPD5926	Approved
0.6094	Remote Similarity	NPD3355	Approved
0.6094	Remote Similarity	NPD3356	Approved
0.609	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD3644	Approved
0.6083	Remote Similarity	NPD3643	Approved
0.6083	Remote Similarity	NPD3642	Approved
0.6071	Remote Similarity	NPD2895	Discontinued
0.6071	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD1761	Approved
0.6068	Remote Similarity	NPD1766	Approved
0.6068	Remote Similarity	NPD1763	Approved
0.6068	Remote Similarity	NPD1767	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