NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.12
Volume:	290.704
LogP:	5.565
LogD:	3.887
LogS:	-4.015
# 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:	0.492
Synthetic Accessibility Score:	2.47
Fsp3:	0.111
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:	-4.941
MDCK Permeability:	1.4793587979511358e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.51
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	97.71337127685547%
Volume Distribution (VD):	0.577
Pgp-substrate:	1.8280503749847412%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.655
CYP2C19-inhibitor:	0.793
CYP2C19-substrate:	0.103
CYP2C9-inhibitor:	0.666
CYP2C9-substrate:	0.823
CYP2D6-inhibitor:	0.739
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.291
CYP3A4-substrate:	0.157

ADMET: Excretion

Clearance (CL):	8.54
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.835
Rat Oral Acute Toxicity:	0.667
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.953
Carcinogencity:	0.887
Eye Corrosion:	0.029
Eye Irritation:	0.969
Respiratory Toxicity:	0.877

Download Data

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

Natural Product: NPC49994

Natural Product ID:	NPC49994
*Common Name:**	12-Deoxytanshinquinone B
IUPAC Name:	8-methyl-2-propan-2-ylphenanthrene-1,4-dione
Synonyms:	12-deoxytanshinquinone b
Standard InCHIKey:	XFSVVSSHBNDWTE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O2/c1-10(2)15-9-16(19)17-13-6-4-5-11(3)12(13)7-8-14(17)18(15)20/h4-10H,1-3H3
SMILES:	CC(C1=CC(=O)c2c(C1=O)ccc1c2cccc1C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227129
PubChem CID:	15484930
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]
NPO13164	Iris hoogiana	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28189	Metzgeria pubescens	Species	Metzgeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14253	Bothriocline longipes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11003	Euphorbia sancta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO191	Amaranthus hybr	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11814	Asphodeline tenuior	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11985	Glycyrrhiza triphylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11487	Senecio madagascariensis	Species	Asteraceae	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	1
NON-MOLECULAR	1
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	=	21600.0	nM	PMID[511186]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	15100.0	nM	PMID[511186]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	10600.0	nM	PMID[511186]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[511186]

☑ 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 NPC49994 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	320
0.1-0.2	1645
0.2-0.3	4405
0.3-0.4	14494
0.4-0.5	13670
0.5-0.6	6945
0.6-0.7	951
0.7-0.8	189
0.8-0.85	37
0.85-0.9	20
0.9-0.95	16
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.957	High Similarity	NPC134882
0.956	High Similarity	NPC238219
0.9462	High Similarity	NPC239185
0.9462	High Similarity	NPC265220
0.9457	High Similarity	NPC260233
0.9451	High Similarity	NPC155232
0.9451	High Similarity	NPC153885
0.9368	High Similarity	NPC109514
0.9368	High Similarity	NPC476993
0.9362	High Similarity	NPC75724
0.9348	High Similarity	NPC289883
0.9341	High Similarity	NPC133461
0.9239	High Similarity	NPC1682
0.9239	High Similarity	NPC188844
0.9231	High Similarity	NPC173413
0.9231	High Similarity	NPC277277
0.9149	High Similarity	NPC185208
0.9149	High Similarity	NPC219573
0.913	High Similarity	NPC284475
0.9121	High Similarity	NPC418308
0.9043	High Similarity	NPC472880
0.9032	High Similarity	NPC59677
0.9032	High Similarity	NPC323420
0.9022	High Similarity	NPC19256
0.9011	High Similarity	NPC157778
0.8901	High Similarity	NPC69057
0.8901	High Similarity	NPC43945
0.8804	High Similarity	NPC267262
0.8791	High Similarity	NPC307
0.8791	High Similarity	NPC160339
0.8776	High Similarity	NPC472879
0.8725	High Similarity	NPC470252
0.86	High Similarity	NPC247976
0.8526	High Similarity	NPC103346
0.8511	High Similarity	NPC298115
0.8462	Intermediate Similarity	NPC215008
0.8396	Intermediate Similarity	NPC470253
0.835	Intermediate Similarity	NPC100767
0.8333	Intermediate Similarity	NPC329282
0.8318	Intermediate Similarity	NPC326664
0.8316	Intermediate Similarity	NPC325709
0.8316	Intermediate Similarity	NPC113307
0.8273	Intermediate Similarity	NPC318173
0.8261	Intermediate Similarity	NPC273758
0.8242	Intermediate Similarity	NPC145053
0.8242	Intermediate Similarity	NPC273033
0.8242	Intermediate Similarity	NPC12936
0.8235	Intermediate Similarity	NPC472691
0.8235	Intermediate Similarity	NPC474866
0.8235	Intermediate Similarity	NPC475939
0.8235	Intermediate Similarity	NPC471829
0.8224	Intermediate Similarity	NPC143768
0.8211	Intermediate Similarity	NPC153308
0.8208	Intermediate Similarity	NPC265513
0.8148	Intermediate Similarity	NPC67377
0.8132	Intermediate Similarity	NPC285716
0.8132	Intermediate Similarity	NPC71664
0.8132	Intermediate Similarity	NPC190567
0.8132	Intermediate Similarity	NPC17408
0.8131	Intermediate Similarity	NPC280789
0.8131	Intermediate Similarity	NPC292834
0.8131	Intermediate Similarity	NPC186128
0.8095	Intermediate Similarity	NPC203732
0.8077	Intermediate Similarity	NPC172483
0.8077	Intermediate Similarity	NPC474910
0.8077	Intermediate Similarity	NPC134120
0.8056	Intermediate Similarity	NPC93287
0.8022	Intermediate Similarity	NPC300205
0.8022	Intermediate Similarity	NPC151405
0.8022	Intermediate Similarity	NPC139901
0.8	Intermediate Similarity	NPC472699
0.8	Intermediate Similarity	NPC164526
0.8	Intermediate Similarity	NPC472700
0.7982	Intermediate Similarity	NPC471721
0.7965	Intermediate Similarity	NPC232958
0.7959	Intermediate Similarity	NPC125226
0.7935	Intermediate Similarity	NPC164086
0.7925	Intermediate Similarity	NPC472695
0.7925	Intermediate Similarity	NPC472696
0.7925	Intermediate Similarity	NPC472701
0.7925	Intermediate Similarity	NPC472683
0.7912	Intermediate Similarity	NPC285470
0.7912	Intermediate Similarity	NPC103488
0.7912	Intermediate Similarity	NPC2785
0.7912	Intermediate Similarity	NPC36342
0.7909	Intermediate Similarity	NPC215419
0.7895	Intermediate Similarity	NPC252067
0.7885	Intermediate Similarity	NPC274443
0.7885	Intermediate Similarity	NPC329556
0.787	Intermediate Similarity	NPC474057
0.7857	Intermediate Similarity	NPC323440
0.7857	Intermediate Similarity	NPC222968
0.7857	Intermediate Similarity	NPC80605
0.7845	Intermediate Similarity	NPC318067
0.7826	Intermediate Similarity	NPC272260
0.7802	Intermediate Similarity	NPC245966
0.7802	Intermediate Similarity	NPC9796
0.7798	Intermediate Similarity	NPC66208
0.7798	Intermediate Similarity	NPC218855
0.7788	Intermediate Similarity	NPC244427
0.7788	Intermediate Similarity	NPC222390
0.7768	Intermediate Similarity	NPC469843
0.7748	Intermediate Similarity	NPC217111
0.7748	Intermediate Similarity	NPC474095
0.7742	Intermediate Similarity	NPC95868
0.7739	Intermediate Similarity	NPC144547
0.7727	Intermediate Similarity	NPC471481
0.7719	Intermediate Similarity	NPC202015
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
0.7658	Intermediate Similarity	NPC130591
0.7658	Intermediate Similarity	NPC234637
0.7658	Intermediate Similarity	NPC196673
0.7652	Intermediate Similarity	NPC988
0.7652	Intermediate Similarity	NPC289432
0.7609	Intermediate Similarity	NPC179726
0.7596	Intermediate Similarity	NPC221825
0.7589	Intermediate Similarity	NPC228936
0.7573	Intermediate Similarity	NPC226041
0.757	Intermediate Similarity	NPC471186
0.7553	Intermediate Similarity	NPC477703
0.7545	Intermediate Similarity	NPC137315
0.7542	Intermediate Similarity	NPC328107
0.7526	Intermediate Similarity	NPC123476
0.7524	Intermediate Similarity	NPC128248
0.7524	Intermediate Similarity	NPC136810
0.7524	Intermediate Similarity	NPC112552
0.7524	Intermediate Similarity	NPC225079
0.7524	Intermediate Similarity	NPC133809
0.7523	Intermediate Similarity	NPC318327
0.7522	Intermediate Similarity	NPC260886
0.75	Intermediate Similarity	NPC58872
0.75	Intermediate Similarity	NPC185763
0.75	Intermediate Similarity	NPC37914
0.75	Intermediate Similarity	NPC83409
0.7476	Intermediate Similarity	NPC12695
0.7474	Intermediate Similarity	NPC73978
0.7474	Intermediate Similarity	NPC100039
0.7456	Intermediate Similarity	NPC158157
0.7447	Intermediate Similarity	NPC159661
0.7438	Intermediate Similarity	NPC478162
0.7438	Intermediate Similarity	NPC478165
0.7436	Intermediate Similarity	NPC472981
0.7434	Intermediate Similarity	NPC93181
0.7434	Intermediate Similarity	NPC186933
0.7431	Intermediate Similarity	NPC470007
0.7429	Intermediate Similarity	NPC476042
0.7414	Intermediate Similarity	NPC476645
0.7411	Intermediate Similarity	NPC13784
0.7407	Intermediate Similarity	NPC167336
0.7404	Intermediate Similarity	NPC240042
0.7404	Intermediate Similarity	NPC103048
0.7404	Intermediate Similarity	NPC156021
0.7391	Intermediate Similarity	NPC268930
0.7391	Intermediate Similarity	NPC61651
0.7387	Intermediate Similarity	NPC291799
0.7377	Intermediate Similarity	NPC96024
0.7373	Intermediate Similarity	NPC167323
0.7373	Intermediate Similarity	NPC269923
0.7368	Intermediate Similarity	NPC135730
0.7368	Intermediate Similarity	NPC157055
0.7363	Intermediate Similarity	NPC54269
0.7363	Intermediate Similarity	NPC285679
0.735	Intermediate Similarity	NPC77000
0.735	Intermediate Similarity	NPC238861
0.7333	Intermediate Similarity	NPC145052
0.7282	Intermediate Similarity	NPC34243
0.7273	Intermediate Similarity	NPC112903
0.7255	Intermediate Similarity	NPC475023
0.7255	Intermediate Similarity	NPC475059
0.7253	Intermediate Similarity	NPC39799
0.7253	Intermediate Similarity	NPC226999
0.7253	Intermediate Similarity	NPC87099
0.7253	Intermediate Similarity	NPC280135
0.7253	Intermediate Similarity	NPC135433
0.7253	Intermediate Similarity	NPC158028
0.7253	Intermediate Similarity	NPC193578
0.7253	Intermediate Similarity	NPC1008
0.7253	Intermediate Similarity	NPC74458
0.725	Intermediate Similarity	NPC51079
0.725	Intermediate Similarity	NPC85511
0.7248	Intermediate Similarity	NPC105899
0.7245	Intermediate Similarity	NPC267704
0.7241	Intermediate Similarity	NPC228318
0.7234	Intermediate Similarity	NPC3190
0.7234	Intermediate Similarity	NPC249018
0.7228	Intermediate Similarity	NPC231591
0.7216	Intermediate Similarity	NPC230068
0.7213	Intermediate Similarity	NPC474106
0.7212	Intermediate Similarity	NPC172925
0.7204	Intermediate Similarity	NPC307195
0.7203	Intermediate Similarity	NPC476225
0.7193	Intermediate Similarity	NPC241851
0.719	Intermediate Similarity	NPC164014
0.719	Intermediate Similarity	NPC295664

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 NPC49994 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	1038
0.2-0.3	1305
0.3-0.4	3313
0.4-0.5	2266
0.5-0.6	751
0.6-0.7	140
0.7-0.8	26
0.8-0.85	2
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9462	High Similarity	NPD3495	Discontinued
0.9239	High Similarity	NPD7631	Approved
0.913	High Similarity	NPD7609	Phase 3
0.8901	High Similarity	NPD650	Approved
0.8438	Intermediate Similarity	NPD1508	Approved
0.8242	Intermediate Similarity	NPD942	Approved
0.8182	Intermediate Similarity	NPD1843	Approved
0.8037	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1932	Approved
0.7885	Intermediate Similarity	NPD1930	Approved
0.7885	Intermediate Similarity	NPD1929	Approved
0.7885	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD2329	Discontinued
0.7767	Intermediate Similarity	NPD2066	Phase 3
0.7742	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD5836	Discontinued
0.7589	Intermediate Similarity	NPD5951	Approved
0.7478	Intermediate Similarity	NPD7009	Phase 2
0.7453	Intermediate Similarity	NPD2648	Phase 3
0.7453	Intermediate Similarity	NPD2193	Phase 2
0.7451	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4879	Approved
0.7391	Intermediate Similarity	NPD7610	Discontinued
0.735	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1989	Approved
0.729	Intermediate Similarity	NPD2196	Discontinued
0.7288	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD1563	Approved
0.7212	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6049	Phase 2
0.7212	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1087	Approved
0.72	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7094	Approved
0.7105	Intermediate Similarity	NPD6858	Approved
0.7087	Intermediate Similarity	NPD1239	Approved
0.7075	Intermediate Similarity	NPD1566	Phase 3
0.7075	Intermediate Similarity	NPD1565	Approved
0.7075	Intermediate Similarity	NPD1564	Approved
0.7054	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1693	Approved
0.7048	Intermediate Similarity	NPD4094	Approved
0.7025	Intermediate Similarity	NPD4878	Approved
0.7	Intermediate Similarity	NPD5909	Discontinued
0.6991	Remote Similarity	NPD1317	Discontinued
0.699	Remote Similarity	NPD1089	Approved
0.699	Remote Similarity	NPD1090	Approved
0.699	Remote Similarity	NPD1086	Approved
0.6972	Remote Similarity	NPD2171	Approved
0.697	Remote Similarity	NPD3971	Phase 1
0.6937	Remote Similarity	NPD1677	Discontinued
0.6937	Remote Similarity	NPD2192	Approved
0.6937	Remote Similarity	NPD2197	Approved
0.6923	Remote Similarity	NPD3317	Approved
0.6916	Remote Similarity	NPD4657	Approved
0.6916	Remote Similarity	NPD4655	Approved
0.6905	Remote Similarity	NPD7008	Discontinued
0.6893	Remote Similarity	NPD800	Approved
0.6857	Remote Similarity	NPD1088	Approved
0.6847	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD1237	Approved
0.6838	Remote Similarity	NPD2508	Discontinued
0.6818	Remote Similarity	NPD6027	Approved
0.6818	Remote Similarity	NPD6024	Approved
0.6792	Remote Similarity	NPD1202	Approved
0.6783	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD2345	Approved
0.6774	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1099	Approved
0.6759	Remote Similarity	NPD1100	Approved
0.6757	Remote Similarity	NPD3357	Discontinued
0.6754	Remote Similarity	NPD2182	Approved
0.6696	Remote Similarity	NPD164	Approved
0.6696	Remote Similarity	NPD664	Approved
0.6667	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7961	Discontinued
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD3672	Approved
0.6641	Remote Similarity	NPD2754	Discontinued
0.664	Remote Similarity	NPD1876	Approved
0.6613	Remote Similarity	NPD3972	Approved
0.6589	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1470	Approved
0.6585	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5346	Phase 2
0.6571	Remote Similarity	NPD5347	Phase 2
0.6562	Remote Similarity	NPD4058	Approved
0.6557	Remote Similarity	NPD1651	Approved
0.6538	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6287	Discontinued
0.6532	Remote Similarity	NPD1201	Approved
0.6529	Remote Similarity	NPD6065	Approved
0.6518	Remote Similarity	NPD813	Approved
0.6504	Remote Similarity	NPD2932	Approved
0.6496	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1238	Approved
0.6484	Remote Similarity	NPD675	Discontinued
0.6471	Remote Similarity	NPD7077	Approved
0.6471	Remote Similarity	NPD7076	Approved
0.6465	Remote Similarity	NPD227	Approved
0.6465	Remote Similarity	NPD225	Approved
0.646	Remote Similarity	NPD5700	Clinical (unspecified phase)
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
0.6429	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	NPD1245	Approved
0.6423	Remote Similarity	NPD3025	Approved
0.6423	Remote Similarity	NPD3024	Approved
0.6423	Remote Similarity	NPD7003	Approved
0.6408	Remote Similarity	NPD4544	Approved
0.6406	Remote Similarity	NPD4980	Approved
0.6406	Remote Similarity	NPD2798	Approved
0.64	Remote Similarity	NPD1281	Approved
0.64	Remote Similarity	NPD9490	Approved
0.6381	Remote Similarity	NPD4793	Discontinued
0.6378	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD3019	Approved
0.637	Remote Similarity	NPD5405	Approved
0.637	Remote Similarity	NPD5404	Approved
0.637	Remote Similarity	NPD5408	Approved
0.637	Remote Similarity	NPD5406	Approved
0.6364	Remote Similarity	NPD3093	Approved
0.6357	Remote Similarity	NPD7084	Phase 3
0.6339	Remote Similarity	NPD7798	Approved
0.6336	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5653	Discontinued
0.6324	Remote Similarity	NPD2346	Discontinued
0.632	Remote Similarity	NPD3023	Approved
0.632	Remote Similarity	NPD3026	Approved
0.6316	Remote Similarity	NPD6647	Phase 2
0.6311	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD9491	Approved
0.6299	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5157	Phase 1
0.6299	Remote Similarity	NPD5159	Phase 2
0.6296	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD7713	Phase 3
0.6281	Remote Similarity	NPD2319	Discontinued
0.6281	Remote Similarity	NPD1246	Approved
0.6275	Remote Similarity	NPD226	Approved
0.626	Remote Similarity	NPD6966	Discovery
0.626	Remote Similarity	NPD997	Clinical (unspecified phase)
0.625	Remote Similarity	NPD466	Approved
0.625	Remote Similarity	NPD4691	Approved
0.625	Remote Similarity	NPD1283	Approved
0.625	Remote Similarity	NPD5926	Approved
0.624	Remote Similarity	NPD4199	Phase 3
0.6224	Remote Similarity	NPD4687	Approved
0.6222	Remote Similarity	NPD4705	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3356	Approved
0.622	Remote Similarity	NPD3355	Approved
0.6216	Remote Similarity	NPD2895	Discontinued
0.6216	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD9256	Approved
0.6204	Remote Similarity	NPD9258	Approved
0.6198	Remote Similarity	NPD6010	Discontinued
0.6183	Remote Similarity	NPD7055	Discontinued
0.6179	Remote Similarity	NPD4574	Approved
0.6179	Remote Similarity	NPD4576	Approved
0.6176	Remote Similarity	NPD3903	Approved
0.6176	Remote Similarity	NPD3979	Approved
0.6176	Remote Similarity	NPD3904	Approved
0.6176	Remote Similarity	NPD3981	Approved
0.6172	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD9716	Approved
0.6161	Remote Similarity	NPD5597	Approved
0.6161	Remote Similarity	NPD5598	Approved
0.6161	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4635	Approved
0.6154	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4137	Phase 3
0.6142	Remote Similarity	NPD5618	Discontinued
0.614	Remote Similarity	NPD6354	Discontinued
0.614	Remote Similarity	NPD5630	Phase 1
0.6136	Remote Similarity	NPD6039	Approved
0.6132	Remote Similarity	NPD3099	Discontinued
0.6124	Remote Similarity	NPD2056	Discontinued
0.6119	Remote Similarity	NPD2979	Phase 3
0.6116	Remote Similarity	NPD7635	Approved
0.6103	Remote Similarity	NPD7541	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4407	Approved
0.6091	Remote Similarity	NPD4405	Approved
0.6091	Remote Similarity	NPD4408	Approved
0.609	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4803	Discontinued
0.6087	Remote Similarity	NPD2010	Phase 3
0.6087	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD3644	Approved
0.6083	Remote Similarity	NPD3643	Approved
0.6083	Remote Similarity	NPD5927	Discontinued

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