NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	764.3
Volume:	745.939
LogP:	2.627
LogD:	1.481
LogS:	-4.606
# Rotatable Bonds:	14
TPSA:	206.1
# H-Bond Aceptor:	14
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.108
Synthetic Accessibility Score:	6.838
Fsp3:	0.683
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.25
MDCK Permeability:	9.790667536435649e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.359
Plasma Protein Binding (PPB):	50.675567626953125%
Volume Distribution (VD):	0.423
Pgp-substrate:	35.01906967163086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.42
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.017
CYP3A4-inhibitor:	0.938
CYP3A4-substrate:	0.579

ADMET: Excretion

Clearance (CL):	7.334
Half-life (T1/2):	0.06

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.895
AMES Toxicity:	0.115
Rat Oral Acute Toxicity:	0.343
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.446
Carcinogencity:	0.214
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC476823

Natural Product ID:	NPC476823
*Common Name:**	Chlorajaponol
IUPAC Name:	1-O-methyl 4-O-[[(1R,2S,7R,9S,10S,12R,13R,14S,17S,19R,20S,21R,23Z)-7,9,21-trihydroxy-23-(1-methoxy-1-oxopropan-2-ylidene)-13,20-dimethyl-9-[[(E)-2-methylbut-2-enoyl]oxymethyl]-4,22-dioxo-3-oxaoctacyclo[14.7.1.02,6.02,14.08,13.010,12.017,19.020,24]tetracosa-5,16(24)-dien-5-yl]methyl] butanedioate
Synonyms:	Chlorajaponol
Standard InCHIKey:	YUXZBKZRBCSMBP-XOFLIZQKSA-N
Standard InCHI:	InChI=1S/C41H48O14/c1-8-16(2)35(47)54-15-40(50)23-13-22(23)38(4)24-12-19-18-11-21(18)39(5)28(19)30(27(31(44)34(39)46)17(3)36(48)52-7)41(24)29(32(45)33(38)40)20(37(49)55-41)14-53-26(43)10-9-25(42)51-6/h8,18,21-24,30,32-34,45-46,50H,9-15H2,1-7H3/b16-8+,27-17-/t18-,21-,22-,23+,24+,30+,32+,33?,34+,38-,39+,40+,41-/m1/s1
SMILES:	C/C=C(\C)/C(=O)OC[C@@]1([C@H]2C[C@H]2[C@]3(C1[C@H](C4=C(C(=O)O[C@]45[C@H]3CC6=C7[C@@H]5/C(=C(\C)/C(=O)OC)/C(=O)[C@@H]([C@]7([C@H]8[C@@H]6C8)C)O)COC(=O)CCC(=O)OC)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	53319120
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1016/j.phytol.2016.01.005]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18451544]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	Whole plant	Suiling district, Heilongjiang Province, China	2008-AUG	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	whole plants	Suiling district, Heilongjiang Province, China	2008-AUG	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21650224]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21650224]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	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	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	<	10000	nM	PMID[21142110]
NPT1997	Cell Line	OS-RC-2	Homo sapiens	IC50	<	10000	nM	PMID[21142110]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	10000	nM	PMID[21142110]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	<	10000	nM	PMID[21142110]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	<	10000	nM	PMID[21142110]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<	10000	nM	PMID[21142110]
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	<	10000	nM	PMID[21142110]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	<	10000	nM	PMID[21142110]

☑ 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 NPC476823 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	311
0.1-0.2	1669
0.2-0.3	4875
0.3-0.4	8090
0.4-0.5	12687
0.5-0.6	7450
0.6-0.7	5678
0.7-0.8	1759
0.8-0.85	125
0.85-0.9	27
0.9-0.95	6
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9918	High Similarity	NPC469673
0.9836	High Similarity	NPC34963
0.9756	High Similarity	NPC58029
0.9754	High Similarity	NPC220757
0.9754	High Similarity	NPC241935
0.9754	High Similarity	NPC279478
0.9754	High Similarity	NPC196921
0.9672	High Similarity	NPC35109
0.9426	High Similarity	NPC15095
0.9016	High Similarity	NPC17938
0.8984	High Similarity	NPC469674
0.8797	High Similarity	NPC25887
0.8731	High Similarity	NPC470426
0.8722	High Similarity	NPC476825
0.8692	High Similarity	NPC327664
0.8692	High Similarity	NPC476097
0.8692	High Similarity	NPC470427
0.8626	High Similarity	NPC60150
0.8626	High Similarity	NPC192334
0.8615	High Similarity	NPC476824
0.8605	High Similarity	NPC231529
0.8583	High Similarity	NPC8374
0.8571	High Similarity	NPC23786
0.8571	High Similarity	NPC470265
0.855	High Similarity	NPC24599
0.8492	Intermediate Similarity	NPC67569
0.8462	Intermediate Similarity	NPC134902
0.8462	Intermediate Similarity	NPC470880
0.845	Intermediate Similarity	NPC470882
0.845	Intermediate Similarity	NPC473253
0.845	Intermediate Similarity	NPC473265
0.8425	Intermediate Similarity	NPC222688
0.8425	Intermediate Similarity	NPC269642
0.8425	Intermediate Similarity	NPC88326
0.8425	Intermediate Similarity	NPC153700
0.8413	Intermediate Similarity	NPC474370
0.8397	Intermediate Similarity	NPC254823
0.8372	Intermediate Similarity	NPC293112
0.8372	Intermediate Similarity	NPC473635
0.8372	Intermediate Similarity	NPC63186
0.8359	Intermediate Similarity	NPC472399
0.8359	Intermediate Similarity	NPC469789
0.8346	Intermediate Similarity	NPC52839
0.8333	Intermediate Similarity	NPC264954
0.8321	Intermediate Similarity	NPC471407
0.832	Intermediate Similarity	NPC239273
0.8308	Intermediate Similarity	NPC287423
0.8295	Intermediate Similarity	NPC172154
0.8295	Intermediate Similarity	NPC81736
0.8295	Intermediate Similarity	NPC8369
0.8293	Intermediate Similarity	NPC470063
0.8281	Intermediate Similarity	NPC162009
0.8281	Intermediate Similarity	NPC19464
0.8281	Intermediate Similarity	NPC257017
0.8268	Intermediate Similarity	NPC471126
0.8268	Intermediate Similarity	NPC471128
0.8268	Intermediate Similarity	NPC145182
0.8268	Intermediate Similarity	NPC157252
0.8268	Intermediate Similarity	NPC472004
0.8254	Intermediate Similarity	NPC311554
0.8254	Intermediate Similarity	NPC257457
0.8254	Intermediate Similarity	NPC50774
0.8254	Intermediate Similarity	NPC709
0.8244	Intermediate Similarity	NPC236999
0.8244	Intermediate Similarity	NPC311534
0.824	Intermediate Similarity	NPC148458
0.8217	Intermediate Similarity	NPC473979
0.8217	Intermediate Similarity	NPC120724
0.8217	Intermediate Similarity	NPC129992
0.8217	Intermediate Similarity	NPC11895
0.8211	Intermediate Similarity	NPC473921
0.8211	Intermediate Similarity	NPC475668
0.8211	Intermediate Similarity	NPC475480
0.8209	Intermediate Similarity	NPC471234
0.8203	Intermediate Similarity	NPC472401
0.8203	Intermediate Similarity	NPC46570
0.8195	Intermediate Similarity	NPC471855
0.8195	Intermediate Similarity	NPC231240
0.8189	Intermediate Similarity	NPC471108
0.8189	Intermediate Similarity	NPC475041
0.8189	Intermediate Similarity	NPC5989
0.8189	Intermediate Similarity	NPC5991
0.8189	Intermediate Similarity	NPC22628
0.8189	Intermediate Similarity	NPC255081
0.8189	Intermediate Similarity	NPC275696
0.8189	Intermediate Similarity	NPC312536
0.8182	Intermediate Similarity	NPC473593
0.8175	Intermediate Similarity	NPC470493
0.8175	Intermediate Similarity	NPC470492
0.8175	Intermediate Similarity	NPC167606
0.8175	Intermediate Similarity	NPC471854
0.8175	Intermediate Similarity	NPC183580
0.8175	Intermediate Similarity	NPC312824
0.8175	Intermediate Similarity	NPC286528
0.8175	Intermediate Similarity	NPC20302
0.8175	Intermediate Similarity	NPC140055
0.8168	Intermediate Similarity	NPC42399
0.8154	Intermediate Similarity	NPC469790
0.8154	Intermediate Similarity	NPC145238
0.8154	Intermediate Similarity	NPC226049
0.8154	Intermediate Similarity	NPC473255
0.8154	Intermediate Similarity	NPC473919
0.8154	Intermediate Similarity	NPC473709
0.8145	Intermediate Similarity	NPC317687
0.814	Intermediate Similarity	NPC170538
0.814	Intermediate Similarity	NPC107493
0.8134	Intermediate Similarity	NPC316915
0.8134	Intermediate Similarity	NPC88668
0.813	Intermediate Similarity	NPC475563
0.813	Intermediate Similarity	NPC475134
0.813	Intermediate Similarity	NPC179642
0.8125	Intermediate Similarity	NPC109973
0.811	Intermediate Similarity	NPC472397
0.811	Intermediate Similarity	NPC118638
0.811	Intermediate Similarity	NPC471125
0.811	Intermediate Similarity	NPC475372
0.811	Intermediate Similarity	NPC186525
0.811	Intermediate Similarity	NPC472758
0.811	Intermediate Similarity	NPC171905
0.8095	Intermediate Similarity	NPC470075
0.8095	Intermediate Similarity	NPC270958
0.8095	Intermediate Similarity	NPC49492
0.8095	Intermediate Similarity	NPC266728
0.808	Intermediate Similarity	NPC202889
0.808	Intermediate Similarity	NPC52634
0.808	Intermediate Similarity	NPC250109
0.808	Intermediate Similarity	NPC477126
0.808	Intermediate Similarity	NPC962
0.8077	Intermediate Similarity	NPC84865
0.8077	Intermediate Similarity	NPC473802
0.8077	Intermediate Similarity	NPC67251
0.8071	Intermediate Similarity	NPC471172
0.8065	Intermediate Similarity	NPC317107
0.8062	Intermediate Similarity	NPC472001
0.8062	Intermediate Similarity	NPC159456
0.8062	Intermediate Similarity	NPC472000
0.8062	Intermediate Similarity	NPC471999
0.8062	Intermediate Similarity	NPC4021
0.806	Intermediate Similarity	NPC476193
0.8049	Intermediate Similarity	NPC284828
0.8049	Intermediate Similarity	NPC173905
0.8049	Intermediate Similarity	NPC5475
0.8049	Intermediate Similarity	NPC472216
0.8047	Intermediate Similarity	NPC472933
0.8047	Intermediate Similarity	NPC61520
0.8047	Intermediate Similarity	NPC469380
0.8047	Intermediate Similarity	NPC477092
0.8045	Intermediate Similarity	NPC104382
0.8045	Intermediate Similarity	NPC476966
0.8033	Intermediate Similarity	NPC67321
0.8033	Intermediate Similarity	NPC187435
0.8031	Intermediate Similarity	NPC243065
0.8031	Intermediate Similarity	NPC475323
0.8031	Intermediate Similarity	NPC472934
0.8031	Intermediate Similarity	NPC473656
0.8031	Intermediate Similarity	NPC10721
0.8031	Intermediate Similarity	NPC156252
0.8031	Intermediate Similarity	NPC284068
0.803	Intermediate Similarity	NPC471357
0.803	Intermediate Similarity	NPC469757
0.803	Intermediate Similarity	NPC117702
0.803	Intermediate Similarity	NPC298841
0.803	Intermediate Similarity	NPC471940
0.803	Intermediate Similarity	NPC146456
0.8016	Intermediate Similarity	NPC67259
0.8016	Intermediate Similarity	NPC147912
0.8016	Intermediate Similarity	NPC178289
0.8016	Intermediate Similarity	NPC474872
0.8015	Intermediate Similarity	NPC3381
0.8015	Intermediate Similarity	NPC470922
0.8015	Intermediate Similarity	NPC476729
0.8015	Intermediate Similarity	NPC24651
0.8014	Intermediate Similarity	NPC48813
0.8014	Intermediate Similarity	NPC194854
0.8	Intermediate Similarity	NPC269530
0.8	Intermediate Similarity	NPC71348
0.8	Intermediate Similarity	NPC100267
0.8	Intermediate Similarity	NPC475524
0.8	Intermediate Similarity	NPC280782
0.7985	Intermediate Similarity	NPC173347
0.7985	Intermediate Similarity	NPC471170
0.7984	Intermediate Similarity	NPC251226
0.7984	Intermediate Similarity	NPC154491
0.7984	Intermediate Similarity	NPC185876
0.7984	Intermediate Similarity	NPC19336
0.7984	Intermediate Similarity	NPC268530
0.797	Intermediate Similarity	NPC470850
0.797	Intermediate Similarity	NPC473620
0.797	Intermediate Similarity	NPC270109
0.7969	Intermediate Similarity	NPC475401
0.7969	Intermediate Similarity	NPC124676
0.7969	Intermediate Similarity	NPC146280
0.7969	Intermediate Similarity	NPC251310
0.7969	Intermediate Similarity	NPC329736
0.7967	Intermediate Similarity	NPC472218
0.7967	Intermediate Similarity	NPC472219
0.7967	Intermediate Similarity	NPC472217
0.7958	Intermediate Similarity	NPC475462
0.7958	Intermediate Similarity	NPC16729
0.7955	Intermediate Similarity	NPC222307

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 NPC476823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	1905
0.2-0.3	3871
0.3-0.4	2029
0.4-0.5	632
0.5-0.6	235
0.6-0.7	142
0.7-0.8	74
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
0.8175	Intermediate Similarity	NPD7115	Discovery
0.7984	Intermediate Similarity	NPD6319	Approved
0.791	Intermediate Similarity	NPD7319	Approved
0.7857	Intermediate Similarity	NPD8297	Approved
0.7778	Intermediate Similarity	NPD6650	Approved
0.7778	Intermediate Similarity	NPD6649	Approved
0.7761	Intermediate Similarity	NPD7078	Approved
0.776	Intermediate Similarity	NPD6373	Approved
0.776	Intermediate Similarity	NPD6372	Approved
0.7744	Intermediate Similarity	NPD7492	Approved
0.771	Intermediate Similarity	NPD6054	Approved
0.7704	Intermediate Similarity	NPD7736	Approved
0.7698	Intermediate Similarity	NPD6371	Approved
0.7698	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6616	Approved
0.7687	Intermediate Similarity	NPD7507	Approved
0.7656	Intermediate Similarity	NPD4632	Approved
0.763	Intermediate Similarity	NPD8293	Discontinued
0.7619	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6370	Approved
0.7576	Intermediate Similarity	NPD6059	Approved
0.7557	Intermediate Similarity	NPD7327	Approved
0.7557	Intermediate Similarity	NPD7328	Approved
0.754	Intermediate Similarity	NPD7320	Approved
0.754	Intermediate Similarity	NPD6881	Approved
0.754	Intermediate Similarity	NPD6899	Approved
0.7537	Intermediate Similarity	NPD7604	Phase 2
0.752	Intermediate Similarity	NPD7128	Approved
0.752	Intermediate Similarity	NPD6402	Approved
0.752	Intermediate Similarity	NPD6675	Approved
0.752	Intermediate Similarity	NPD5739	Approved
0.7519	Intermediate Similarity	NPD8033	Approved
0.7519	Intermediate Similarity	NPD8296	Approved
0.7519	Intermediate Similarity	NPD8378	Approved
0.7519	Intermediate Similarity	NPD6015	Approved
0.7519	Intermediate Similarity	NPD8380	Approved
0.7519	Intermediate Similarity	NPD6016	Approved
0.7519	Intermediate Similarity	NPD8335	Approved
0.7519	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD7516	Approved
0.7463	Intermediate Similarity	NPD5988	Approved
0.746	Intermediate Similarity	NPD5697	Approved
0.746	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8377	Approved
0.7444	Intermediate Similarity	NPD8294	Approved
0.7442	Intermediate Similarity	NPD6882	Approved
0.7422	Intermediate Similarity	NPD7102	Approved
0.7422	Intermediate Similarity	NPD4634	Approved
0.7422	Intermediate Similarity	NPD6883	Approved
0.7422	Intermediate Similarity	NPD7290	Approved
0.7398	Intermediate Similarity	NPD7639	Approved
0.7398	Intermediate Similarity	NPD7640	Approved
0.7381	Intermediate Similarity	NPD6008	Approved
0.7364	Intermediate Similarity	NPD6869	Approved
0.7364	Intermediate Similarity	NPD6847	Approved
0.7364	Intermediate Similarity	NPD6617	Approved
0.7348	Intermediate Similarity	NPD6009	Approved
0.7344	Intermediate Similarity	NPD6013	Approved
0.7344	Intermediate Similarity	NPD6014	Approved
0.7344	Intermediate Similarity	NPD6012	Approved
0.7323	Intermediate Similarity	NPD5701	Approved
0.7317	Intermediate Similarity	NPD7638	Approved
0.7317	Intermediate Similarity	NPD4225	Approved
0.728	Intermediate Similarity	NPD5211	Phase 2
0.7266	Intermediate Similarity	NPD6011	Approved
0.7266	Intermediate Similarity	NPD6686	Approved
0.7266	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5983	Phase 2
0.7236	Intermediate Similarity	NPD6084	Phase 2
0.7236	Intermediate Similarity	NPD6083	Phase 2
0.7174	Intermediate Similarity	NPD6336	Discontinued
0.7165	Intermediate Similarity	NPD5141	Approved
0.7153	Intermediate Similarity	NPD8328	Phase 3
0.7132	Intermediate Similarity	NPD7503	Approved
0.712	Intermediate Similarity	NPD4696	Approved
0.712	Intermediate Similarity	NPD5285	Approved
0.712	Intermediate Similarity	NPD5286	Approved
0.7099	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4755	Approved
0.7073	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6033	Approved
0.7054	Intermediate Similarity	NPD6412	Phase 2
0.7049	Intermediate Similarity	NPD6399	Phase 3
0.7045	Intermediate Similarity	NPD6053	Discontinued
0.704	Intermediate Similarity	NPD5696	Approved
0.7015	Intermediate Similarity	NPD6274	Approved
0.7008	Intermediate Similarity	NPD4633	Approved
0.7008	Intermediate Similarity	NPD5226	Approved
0.7008	Intermediate Similarity	NPD5224	Approved
0.7008	Intermediate Similarity	NPD5225	Approved
0.6992	Remote Similarity	NPD6001	Approved
0.6985	Remote Similarity	NPD7100	Approved
0.6985	Remote Similarity	NPD7101	Approved
0.6984	Remote Similarity	NPD4700	Approved
0.6953	Remote Similarity	NPD5174	Approved
0.6953	Remote Similarity	NPD5175	Approved
0.6935	Remote Similarity	NPD5695	Phase 3
0.6929	Remote Similarity	NPD5344	Discontinued
0.6929	Remote Similarity	NPD5223	Approved
0.6912	Remote Similarity	NPD6335	Approved
0.6884	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7632	Discontinued
0.687	Remote Similarity	NPD4729	Approved
0.687	Remote Similarity	NPD4730	Approved
0.6866	Remote Similarity	NPD8133	Approved
0.6846	Remote Similarity	NPD4767	Approved
0.6846	Remote Similarity	NPD4768	Approved
0.6838	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6317	Approved
0.6829	Remote Similarity	NPD5693	Phase 1
0.6825	Remote Similarity	NPD7902	Approved
0.6818	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4753	Phase 2
0.68	Remote Similarity	NPD4629	Approved
0.68	Remote Similarity	NPD5210	Approved
0.6788	Remote Similarity	NPD6313	Approved
0.6788	Remote Similarity	NPD6314	Approved
0.6774	Remote Similarity	NPD4202	Approved
0.6767	Remote Similarity	NPD5250	Approved
0.6767	Remote Similarity	NPD5251	Approved
0.6767	Remote Similarity	NPD5249	Phase 3
0.6767	Remote Similarity	NPD5248	Approved
0.6767	Remote Similarity	NPD5247	Approved
0.6763	Remote Similarity	NPD8513	Phase 3
0.6763	Remote Similarity	NPD8515	Approved
0.6763	Remote Similarity	NPD6908	Approved
0.6763	Remote Similarity	NPD6909	Approved
0.6763	Remote Similarity	NPD6921	Approved
0.6763	Remote Similarity	NPD8517	Approved
0.6763	Remote Similarity	NPD8516	Approved
0.6748	Remote Similarity	NPD5785	Approved
0.6746	Remote Similarity	NPD4697	Phase 3
0.6742	Remote Similarity	NPD5128	Approved
0.6736	Remote Similarity	NPD5956	Approved
0.6692	Remote Similarity	NPD4754	Approved
0.669	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6644	Remote Similarity	NPD6333	Approved
0.6644	Remote Similarity	NPD6334	Approved
0.6619	Remote Similarity	NPD4522	Approved
0.6614	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5221	Approved
0.6614	Remote Similarity	NPD5222	Approved
0.6613	Remote Similarity	NPD6698	Approved
0.6613	Remote Similarity	NPD46	Approved
0.6593	Remote Similarity	NPD5217	Approved
0.6593	Remote Similarity	NPD5216	Approved
0.6593	Remote Similarity	NPD5215	Approved
0.6593	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD6648	Approved
0.6587	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7748	Approved
0.6587	Remote Similarity	NPD7900	Approved
0.6585	Remote Similarity	NPD5737	Approved
0.6585	Remote Similarity	NPD6672	Approved
0.6585	Remote Similarity	NPD6903	Approved
0.6562	Remote Similarity	NPD5173	Approved
0.656	Remote Similarity	NPD8034	Phase 2
0.656	Remote Similarity	NPD8035	Phase 2
0.656	Remote Similarity	NPD6079	Approved
0.656	Remote Similarity	NPD7637	Suspended
0.6557	Remote Similarity	NPD6409	Approved
0.6557	Remote Similarity	NPD7521	Approved
0.6557	Remote Similarity	NPD7334	Approved
0.6557	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5330	Approved
0.6557	Remote Similarity	NPD3618	Phase 1
0.6557	Remote Similarity	NPD6684	Approved
0.6557	Remote Similarity	NPD7146	Approved
0.6549	Remote Similarity	NPD6067	Discontinued
0.6532	Remote Similarity	NPD5328	Approved
0.6531	Remote Similarity	NPD6845	Suspended
0.6528	Remote Similarity	NPD8074	Phase 3
0.6522	Remote Similarity	NPD6868	Approved
0.6519	Remote Similarity	NPD5135	Approved
0.6519	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5169	Approved
0.6509	Remote Similarity	NPD7799	Discontinued
0.6475	Remote Similarity	NPD5329	Approved
0.6471	Remote Similarity	NPD5127	Approved
0.6457	Remote Similarity	NPD5282	Discontinued
0.6452	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7515	Phase 2
0.6429	Remote Similarity	NPD5284	Approved
0.6429	Remote Similarity	NPD6050	Approved
0.6429	Remote Similarity	NPD5281	Approved
0.6423	Remote Similarity	NPD6098	Approved
0.6412	Remote Similarity	NPD1700	Approved
0.6406	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD3666	Approved
0.6393	Remote Similarity	NPD4197	Approved
0.6393	Remote Similarity	NPD4786	Approved
0.6393	Remote Similarity	NPD3133	Approved
0.6393	Remote Similarity	NPD3665	Phase 1
0.6385	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7838	Discovery

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