NPASS Compound

Structure

NPC25361 OpenBabel07101719512D 24 26 0 0 1 0 0 0 0 0999 V2000 1.7321 2.0000 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 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 -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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 12 2 0 0 0 0 8 1 1 1 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 2 1 6 0 0 0 9 24 1 0 0 0 0 10 21 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.13
Volume:	331.137
LogP:	3.847
LogD:	3.04
LogS:	-4.911
# Rotatable Bonds:	3
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.93
Synthetic Accessibility Score:	3.441
Fsp3:	0.389
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.684
MDCK Permeability:	2.948270230263006e-05
Pgp-inhibitor:	0.957
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	88.46227264404297%
Volume Distribution (VD):	0.792
Pgp-substrate:	10.062288284301758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.903
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.646
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.536
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.717
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.648
CYP3A4-substrate:	0.62

ADMET: Excretion

Clearance (CL):	6.639
Half-life (T1/2):	0.182

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.291
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.112
Skin Sensitization:	0.662
Carcinogencity:	0.065
Eye Corrosion:	0.003
Eye Irritation:	0.554
Respiratory Toxicity:	0.688

Download Data

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

Natural Product: NPC25361

Natural Product ID:	NPC25361
*Common Name:**	(2S,3S)-5-Hydroxy-6,8,10-Trimethoxy-2,3-Dimethyl-2,3-Dihydrobenzo[G]Chromen-4-One
IUPAC Name:	(2S,3S)-5-hydroxy-6,8,10-trimethoxy-2,3-dimethyl-2,3-dihydrobenzo[g]chromen-4-one
Synonyms:
Standard InCHIKey:	KRQMXQZQIPIILU-IUCAKERBSA-N
Standard InCHI:	InChI=1S/C18H20O6/c1-8-9(2)24-18-14(15(8)19)16(20)13-11(17(18)23-5)6-10(21-3)7-12(13)22-4/h6-9,20H,1-5H3/t8-,9-/m0/s1
SMILES:	C[C@H]1[C@H](C)Oc2c(C1=O)c(c1c(cc(cc1OC)OC)c2OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497708
PubChem CID:	10544539
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO4343	Guanomyces polythrix	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[10869195]
NPO4343	Guanomyces polythrix	Species	n.a.	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	65000.0	nM	PMID[452586]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	61000.0	nM	PMID[452586]

☑ 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 NPC25361 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	435
0.1-0.2	1648
0.2-0.3	3862
0.3-0.4	9505
0.4-0.5	8933
0.5-0.6	3372
0.6-0.7	4901
0.7-0.8	5609
0.8-0.85	2773
0.85-0.9	1378
0.9-0.95	277
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC197168
0.9679	High Similarity	NPC66288
0.9679	High Similarity	NPC474186
0.9615	High Similarity	NPC475886
0.9615	High Similarity	NPC474287
0.9613	High Similarity	NPC217677
0.9613	High Similarity	NPC165977
0.9557	High Similarity	NPC270837
0.9557	High Similarity	NPC236132
0.9554	High Similarity	NPC474351
0.9554	High Similarity	NPC474187
0.9554	High Similarity	NPC475883
0.9497	High Similarity	NPC326520
0.9494	High Similarity	NPC294965
0.949	High Similarity	NPC56085
0.949	High Similarity	NPC228785
0.949	High Similarity	NPC14353
0.9437	High Similarity	NPC170245
0.9434	High Similarity	NPC273959
0.9434	High Similarity	NPC7483
0.943	High Similarity	NPC40491
0.943	High Similarity	NPC278052
0.943	High Similarity	NPC61010
0.9427	High Similarity	NPC85121
0.9427	High Similarity	NPC100123
0.9379	High Similarity	NPC117854
0.9379	High Similarity	NPC477154
0.9379	High Similarity	NPC6588
0.9371	High Similarity	NPC229632
0.9367	High Similarity	NPC320359
0.9367	High Similarity	NPC299436
0.9367	High Similarity	NPC119224
0.9367	High Similarity	NPC36217
0.9363	High Similarity	NPC223787
0.9363	High Similarity	NPC469584
0.9363	High Similarity	NPC300727
0.9363	High Similarity	NPC181960
0.9363	High Similarity	NPC241904
0.9359	High Similarity	NPC37392
0.9359	High Similarity	NPC472909
0.9355	High Similarity	NPC87708
0.9317	High Similarity	NPC120593
0.9317	High Similarity	NPC43319
0.9317	High Similarity	NPC37870
0.9317	High Similarity	NPC272502
0.9313	High Similarity	NPC236521
0.9313	High Similarity	NPC152659
0.9313	High Similarity	NPC475985
0.9313	High Similarity	NPC474350
0.9313	High Similarity	NPC248638
0.9313	High Similarity	NPC220313
0.9308	High Similarity	NPC266314
0.9304	High Similarity	NPC250214
0.9304	High Similarity	NPC95936
0.9304	High Similarity	NPC329091
0.9304	High Similarity	NPC476242
0.9299	High Similarity	NPC274730
0.9299	High Similarity	NPC142339
0.929	High Similarity	NPC72958
0.929	High Similarity	NPC232645
0.9259	High Similarity	NPC225419
0.9259	High Similarity	NPC474024
0.9259	High Similarity	NPC218226
0.9255	High Similarity	NPC472450
0.9255	High Similarity	NPC239752
0.9255	High Similarity	NPC275780
0.9255	High Similarity	NPC473286
0.925	High Similarity	NPC52204
0.925	High Similarity	NPC201800
0.925	High Similarity	NPC25152
0.925	High Similarity	NPC470694
0.9241	High Similarity	NPC162869
0.9241	High Similarity	NPC236796
0.9241	High Similarity	NPC156057
0.9241	High Similarity	NPC474208
0.9241	High Similarity	NPC472911
0.9241	High Similarity	NPC472913
0.9241	High Similarity	NPC48208
0.9241	High Similarity	NPC96167
0.9241	High Similarity	NPC78225
0.9241	High Similarity	NPC472914
0.9241	High Similarity	NPC222814
0.9241	High Similarity	NPC262286
0.9241	High Similarity	NPC36852
0.9241	High Similarity	NPC475267
0.9241	High Similarity	NPC474836
0.9241	High Similarity	NPC472910
0.9241	High Similarity	NPC245758
0.9236	High Similarity	NPC45849
0.9236	High Similarity	NPC200761
0.9236	High Similarity	NPC31018
0.9236	High Similarity	NPC255807
0.9236	High Similarity	NPC226025
0.9236	High Similarity	NPC470327
0.9236	High Similarity	NPC477503
0.9226	High Similarity	NPC338131
0.9217	High Similarity	NPC246877
0.9212	High Similarity	NPC289147
0.9207	High Similarity	NPC4200
0.9202	High Similarity	NPC99613
0.9202	High Similarity	NPC49487
0.9198	High Similarity	NPC29160
0.9198	High Similarity	NPC39091
0.9198	High Similarity	NPC128293
0.9198	High Similarity	NPC472452
0.9193	High Similarity	NPC23298
0.9193	High Similarity	NPC189473
0.9193	High Similarity	NPC186686
0.9193	High Similarity	NPC207690
0.9193	High Similarity	NPC474240
0.9193	High Similarity	NPC41301
0.9193	High Similarity	NPC156082
0.9187	High Similarity	NPC32694
0.9182	High Similarity	NPC186113
0.9182	High Similarity	NPC210459
0.9177	High Similarity	NPC470328
0.9177	High Similarity	NPC235165
0.9177	High Similarity	NPC209614
0.9177	High Similarity	NPC195796
0.9177	High Similarity	NPC164427
0.9177	High Similarity	NPC191146
0.9177	High Similarity	NPC35038
0.9177	High Similarity	NPC255106
0.9177	High Similarity	NPC68093
0.9177	High Similarity	NPC278778
0.9177	High Similarity	NPC291878
0.9177	High Similarity	NPC472626
0.9177	High Similarity	NPC138243
0.9172	High Similarity	NPC472915
0.9172	High Similarity	NPC280937
0.9172	High Similarity	NPC89474
0.9172	High Similarity	NPC135522
0.9167	High Similarity	NPC117579
0.9146	High Similarity	NPC239440
0.9146	High Similarity	NPC20543
0.9141	High Similarity	NPC234331
0.9136	High Similarity	NPC293319
0.9136	High Similarity	NPC475888
0.9136	High Similarity	NPC112981
0.913	High Similarity	NPC473961
0.913	High Similarity	NPC81679
0.913	High Similarity	NPC211107
0.913	High Similarity	NPC474150
0.913	High Similarity	NPC215612
0.913	High Similarity	NPC474162
0.9125	High Similarity	NPC235018
0.9125	High Similarity	NPC45146
0.9125	High Similarity	NPC470810
0.9125	High Similarity	NPC155302
0.9125	High Similarity	NPC161947
0.9125	High Similarity	NPC200746
0.9125	High Similarity	NPC321399
0.9125	High Similarity	NPC84571
0.9119	High Similarity	NPC476981
0.9119	High Similarity	NPC129684
0.9119	High Similarity	NPC284820
0.9119	High Similarity	NPC99597
0.9119	High Similarity	NPC27337
0.9119	High Similarity	NPC210084
0.9119	High Similarity	NPC136674
0.9119	High Similarity	NPC299520
0.9119	High Similarity	NPC473272
0.9119	High Similarity	NPC472598
0.9119	High Similarity	NPC291508
0.9119	High Similarity	NPC474055
0.9114	High Similarity	NPC67396
0.9114	High Similarity	NPC175192
0.9114	High Similarity	NPC113906
0.9108	High Similarity	NPC106976
0.9108	High Similarity	NPC474843
0.9103	High Similarity	NPC202595
0.9103	High Similarity	NPC227122
0.9103	High Similarity	NPC179183
0.9091	High Similarity	NPC260263
0.9091	High Similarity	NPC158226
0.9085	High Similarity	NPC163130
0.9085	High Similarity	NPC165979
0.9085	High Similarity	NPC300307
0.9085	High Similarity	NPC476637
0.908	High Similarity	NPC20216
0.908	High Similarity	NPC472449
0.908	High Similarity	NPC173292
0.9074	High Similarity	NPC146134
0.9074	High Similarity	NPC329669
0.9074	High Similarity	NPC18100
0.9074	High Similarity	NPC472278
0.9074	High Similarity	NPC473313
0.9068	High Similarity	NPC474239
0.9068	High Similarity	NPC472275
0.9068	High Similarity	NPC278427
0.9068	High Similarity	NPC87431
0.9068	High Similarity	NPC311740
0.9068	High Similarity	NPC134783
0.9062	High Similarity	NPC473990
0.9062	High Similarity	NPC235448
0.9062	High Similarity	NPC152904
0.9057	High Similarity	NPC24640
0.9057	High Similarity	NPC472916
0.9051	High Similarity	NPC74924
0.9051	High Similarity	NPC298692

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 NPC25361 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	978
0.2-0.3	1824
0.3-0.4	2594
0.4-0.5	1802
0.5-0.6	916
0.6-0.7	451
0.7-0.8	157
0.8-0.85	32
0.85-0.9	10
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9051	High Similarity	NPD2393	Clinical (unspecified phase)
0.9006	High Similarity	NPD5494	Approved
0.8987	High Similarity	NPD1934	Approved
0.897	High Similarity	NPD5844	Phase 1
0.8963	High Similarity	NPD7473	Discontinued
0.8931	High Similarity	NPD2801	Approved
0.8896	High Similarity	NPD6232	Discontinued
0.8834	High Similarity	NPD6959	Discontinued
0.8563	High Similarity	NPD6168	Clinical (unspecified phase)
0.8563	High Similarity	NPD6167	Clinical (unspecified phase)
0.8563	High Similarity	NPD6166	Phase 2
0.8476	Intermediate Similarity	NPD3882	Suspended
0.8466	Intermediate Similarity	NPD7819	Suspended
0.8428	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD4380	Phase 2
0.8365	Intermediate Similarity	NPD1511	Approved
0.8364	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD7074	Phase 3
0.8353	Intermediate Similarity	NPD3818	Discontinued
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD2534	Approved
0.8313	Intermediate Similarity	NPD2533	Approved
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD2532	Approved
0.8304	Intermediate Similarity	NPD7054	Approved
0.8303	Intermediate Similarity	NPD3817	Phase 2
0.828	Intermediate Similarity	NPD1549	Phase 2
0.8261	Intermediate Similarity	NPD1512	Approved
0.8256	Intermediate Similarity	NPD7472	Approved
0.8242	Intermediate Similarity	NPD1465	Phase 2
0.8242	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD1247	Approved
0.8161	Intermediate Similarity	NPD6559	Discontinued
0.8146	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD7808	Phase 3
0.8103	Intermediate Similarity	NPD6797	Phase 2
0.8095	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7251	Discontinued
0.805	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2796	Approved
0.8012	Intermediate Similarity	NPD7411	Suspended
0.7989	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1510	Phase 2
0.7964	Intermediate Similarity	NPD6801	Discontinued
0.7964	Intermediate Similarity	NPD37	Approved
0.7962	Intermediate Similarity	NPD1607	Approved
0.7956	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6599	Discontinued
0.7941	Intermediate Similarity	NPD6234	Discontinued
0.7929	Intermediate Similarity	NPD4966	Approved
0.7929	Intermediate Similarity	NPD4967	Phase 2
0.7929	Intermediate Similarity	NPD4965	Approved
0.7925	Intermediate Similarity	NPD6100	Approved
0.7925	Intermediate Similarity	NPD6099	Approved
0.7919	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7390	Discontinued
0.7898	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3226	Approved
0.7888	Intermediate Similarity	NPD2800	Approved
0.7882	Intermediate Similarity	NPD3749	Approved
0.7875	Intermediate Similarity	NPD2346	Discontinued
0.787	Intermediate Similarity	NPD5402	Approved
0.7861	Intermediate Similarity	NPD3926	Phase 2
0.7849	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD919	Approved
0.7834	Intermediate Similarity	NPD1240	Approved
0.7824	Intermediate Similarity	NPD7768	Phase 2
0.7812	Intermediate Similarity	NPD2935	Discontinued
0.7805	Intermediate Similarity	NPD6799	Approved
0.7803	Intermediate Similarity	NPD5711	Approved
0.7803	Intermediate Similarity	NPD5710	Approved
0.7765	Intermediate Similarity	NPD8312	Approved
0.7765	Intermediate Similarity	NPD8313	Approved
0.7758	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD3750	Approved
0.7727	Intermediate Similarity	NPD7228	Approved
0.7727	Intermediate Similarity	NPD3751	Discontinued
0.7701	Intermediate Similarity	NPD3787	Discontinued
0.768	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6776	Approved
0.766	Intermediate Similarity	NPD6782	Approved
0.766	Intermediate Similarity	NPD6781	Approved
0.766	Intermediate Similarity	NPD6778	Approved
0.766	Intermediate Similarity	NPD6780	Approved
0.766	Intermediate Similarity	NPD6779	Approved
0.766	Intermediate Similarity	NPD6777	Approved
0.7644	Intermediate Similarity	NPD7199	Phase 2
0.7643	Intermediate Similarity	NPD4625	Phase 3
0.7637	Intermediate Similarity	NPD8150	Discontinued
0.7622	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7617	Intermediate Similarity	NPD8151	Discontinued
0.761	Intermediate Similarity	NPD1613	Approved
0.761	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD943	Approved
0.7593	Intermediate Similarity	NPD1551	Phase 2
0.7561	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD920	Approved
0.7557	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD7696	Phase 3
0.7539	Intermediate Similarity	NPD7435	Discontinued
0.7539	Intermediate Similarity	NPD7698	Approved
0.7539	Intermediate Similarity	NPD7697	Approved
0.7538	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7783	Phase 2
0.7531	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD6651	Approved
0.7516	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7870	Phase 2
0.75	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD7229	Phase 3
0.7484	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5403	Approved
0.7456	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1243	Approved
0.7453	Intermediate Similarity	NPD230	Phase 1
0.7453	Intermediate Similarity	NPD447	Suspended
0.7446	Intermediate Similarity	NPD8434	Phase 2
0.744	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2344	Approved
0.7423	Intermediate Similarity	NPD3748	Approved
0.7423	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD3027	Phase 3
0.7403	Intermediate Similarity	NPD5953	Discontinued
0.7396	Intermediate Similarity	NPD6823	Phase 2
0.7394	Intermediate Similarity	NPD4360	Phase 2
0.7394	Intermediate Similarity	NPD6535	Approved
0.7394	Intermediate Similarity	NPD4363	Phase 3
0.7394	Intermediate Similarity	NPD6534	Approved
0.7389	Intermediate Similarity	NPD7286	Phase 2
0.7385	Intermediate Similarity	NPD7701	Phase 2
0.7375	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7240	Approved
0.736	Intermediate Similarity	NPD7801	Approved
0.7358	Intermediate Similarity	NPD4908	Phase 1
0.7349	Intermediate Similarity	NPD6674	Discontinued
0.7337	Intermediate Similarity	NPD5401	Approved
0.7321	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1653	Approved
0.731	Intermediate Similarity	NPD7874	Approved
0.7296	Intermediate Similarity	NPD2861	Phase 2
0.7283	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7700	Phase 2
0.7277	Intermediate Similarity	NPD7699	Phase 2
0.7273	Intermediate Similarity	NPD5406	Approved
0.7273	Intermediate Similarity	NPD5404	Approved
0.7273	Intermediate Similarity	NPD5405	Approved
0.7273	Intermediate Similarity	NPD5408	Approved
0.7267	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2313	Discontinued
0.7267	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2309	Approved
0.7261	Intermediate Similarity	NPD4749	Approved
0.7257	Intermediate Similarity	NPD5353	Approved
0.7246	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1610	Phase 2
0.7239	Intermediate Similarity	NPD1933	Approved
0.7202	Intermediate Similarity	NPD7003	Approved
0.7202	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4060	Phase 1
0.7174	Intermediate Similarity	NPD7685	Pre-registration
0.717	Intermediate Similarity	NPD1470	Approved
0.7169	Intermediate Similarity	NPD2438	Suspended
0.7167	Intermediate Similarity	NPD5242	Approved
0.716	Intermediate Similarity	NPD6190	Approved
0.7158	Intermediate Similarity	NPD6213	Phase 3
0.7158	Intermediate Similarity	NPD6212	Phase 3
0.7158	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD7177	Discontinued
0.7134	Intermediate Similarity	NPD1201	Approved
0.7134	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD2403	Approved
0.7108	Intermediate Similarity	NPD4111	Phase 1
0.7108	Intermediate Similarity	NPD4665	Approved
0.7107	Intermediate Similarity	NPD1283	Approved
0.7102	Intermediate Similarity	NPD5760	Phase 2
0.7102	Intermediate Similarity	NPD5761	Phase 2
0.7093	Intermediate Similarity	NPD6273	Approved
0.7083	Intermediate Similarity	NPD4361	Phase 2
0.7083	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD9494	Approved
0.7073	Intermediate Similarity	NPD2979	Phase 3
0.7059	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8320	Phase 1
0.7056	Intermediate Similarity	NPD8319	Approved
0.7055	Intermediate Similarity	NPD3268	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