NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	560.2
Volume:	566.72
LogP:	3.644
LogD:	3.421
LogS:	-3.647
# Rotatable Bonds:	8
TPSA:	149.07
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.181
Synthetic Accessibility Score:	4.049
Fsp3:	0.25
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.865
MDCK Permeability:	7.61E-06
Pgp-inhibitor:	0.069
Pgp-substrate:	0.077
Human Intestinal Absorption (HIA):	0.575
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	99.78%
Volume Distribution (VD):	0.448
Pgp-substrate:	2.08%

ADMET: Metabolism

CYP1A2-inhibitor:	0.159
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.579
CYP2C19-substrate:	0.116
CYP2C9-inhibitor:	0.834
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.379
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.391
CYP3A4-substrate:	0.884

ADMET: Excretion

Clearance (CL):	12.783
Half-life (T1/2):	0.606

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.211
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.701
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.952
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.862
Respiratory Toxicity:	0.078

Download Data

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

Natural Product: NPC477612

Natural Product ID:	NPC477612
*Common Name:**	Oxytropisoflavan A
IUPAC Name:	4-[2-hydroxy-1-[(3R)-7-hydroxy-3-(2-hydroxy-3,4-dimethoxyphenyl)-3,4-dihydro-2H-chromen-6-yl]-3-(4-hydroxyphenyl)propyl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	KXVXSZGCAQDLCQ-JYAATUFISA-N
Standard InCHI:	InChI=1S/C32H32O9/c1-39-28-10-9-22(31(38)32(28)40-2)19-12-18-13-24(26(36)15-29(18)41-16-19)30(23-8-7-21(34)14-25(23)35)27(37)11-17-3-5-20(33)6-4-17/h3-10,13-15,19,27,30,33-38H,11-12,16H2,1-2H3/t19-,27?,30?/m0/s1
SMILES:	COC1=C(C(=C(C=C1)[C@H]2CC3=CC(=C(C=C3OC2)O)C(C4=C(C=C(C=C4)O)O)C(CC5=CC=C(C=C5)O)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	46918733
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids

*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
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	Sunan County, Gansu Province, China	2006-JUN	PMID[20684529]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	whole plant	Guide County, Qinghai Province, China	2008-AUG	PMID[22775441]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000	nM	PMID[20684529]
NPT1	Others	Radical scavenging activity		IC20	>	50	nM	PMID[20684529]

☑ 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 NPC477612 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	485
0.1-0.2	1594
0.2-0.3	4406
0.3-0.4	11181
0.4-0.5	7195
0.5-0.6	4136
0.6-0.7	6117
0.7-0.8	5842
0.8-0.85	986
0.85-0.9	554
0.9-0.95	176
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.979	High Similarity	NPC211561
0.965	High Similarity	NPC70409
0.965	High Similarity	NPC58190
0.965	High Similarity	NPC294558
0.965	High Similarity	NPC262911
0.965	High Similarity	NPC236202
0.965	High Similarity	NPC82917
0.965	High Similarity	NPC202742
0.965	High Similarity	NPC170103
0.965	High Similarity	NPC204770
0.965	High Similarity	NPC108811
0.965	High Similarity	NPC263940
0.965	High Similarity	NPC18185
0.9589	High Similarity	NPC226809
0.9589	High Similarity	NPC279406
0.9583	High Similarity	NPC227516
0.9583	High Similarity	NPC20757
0.958	High Similarity	NPC96576
0.9524	High Similarity	NPC224161
0.9459	High Similarity	NPC46335
0.9448	High Similarity	NPC281549
0.9444	High Similarity	NPC260397
0.9441	High Similarity	NPC28440
0.9441	High Similarity	NPC171932
0.9388	High Similarity	NPC321972
0.9388	High Similarity	NPC324517
0.9388	High Similarity	NPC329343
0.9384	High Similarity	NPC321657
0.9384	High Similarity	NPC318373
0.9384	High Similarity	NPC476969
0.9375	High Similarity	NPC181615
0.9366	High Similarity	NPC178054
0.9329	High Similarity	NPC157333
0.9324	High Similarity	NPC272552
0.9324	High Similarity	NPC322899
0.9324	High Similarity	NPC46283
0.9324	High Similarity	NPC226108
0.9324	High Similarity	NPC44192
0.9324	High Similarity	NPC469944
0.9324	High Similarity	NPC134911
0.9296	High Similarity	NPC291101
0.9296	High Similarity	NPC266197
0.9296	High Similarity	NPC262189
0.9296	High Similarity	NPC22317
0.9272	High Similarity	NPC147743
0.9272	High Similarity	NPC4809
0.9272	High Similarity	NPC470827
0.9272	High Similarity	NPC73517
0.9262	High Similarity	NPC306267
0.9262	High Similarity	NPC20050
0.9252	High Similarity	NPC470826
0.9252	High Similarity	NPC470098
0.9252	High Similarity	NPC473266
0.9247	High Similarity	NPC327412
0.9247	High Similarity	NPC320970
0.9247	High Similarity	NPC320671
0.9247	High Similarity	NPC328567
0.9231	High Similarity	NPC277331
0.9231	High Similarity	NPC100482
0.9225	High Similarity	NPC70682
0.9225	High Similarity	NPC260741
0.9211	High Similarity	NPC106601
0.9211	High Similarity	NPC470828
0.9211	High Similarity	NPC151474
0.9211	High Similarity	NPC86630
0.9211	High Similarity	NPC212614
0.9211	High Similarity	NPC205613
0.9211	High Similarity	NPC471404
0.9211	High Similarity	NPC185231
0.9211	High Similarity	NPC159526
0.9195	High Similarity	NPC157783
0.9178	High Similarity	NPC317053
0.9178	High Similarity	NPC324492
0.9172	High Similarity	NPC473108
0.9172	High Similarity	NPC475492
0.9167	High Similarity	NPC2613
0.9167	High Similarity	NPC475891
0.9167	High Similarity	NPC204347
0.9167	High Similarity	NPC59841
0.9155	High Similarity	NPC474390
0.9155	High Similarity	NPC470307
0.9155	High Similarity	NPC470308
0.9145	High Similarity	NPC125495
0.9139	High Similarity	NPC202104
0.9128	High Similarity	NPC302915
0.9128	High Similarity	NPC2745
0.9116	High Similarity	NPC262297
0.9097	High Similarity	NPC470372
0.9097	High Similarity	NPC87725
0.9097	High Similarity	NPC263261
0.9097	High Similarity	NPC35216
0.9097	High Similarity	NPC471389
0.9091	High Similarity	NPC22517
0.9085	High Similarity	NPC471522
0.9085	High Similarity	NPC265433
0.9085	High Similarity	NPC306441
0.9085	High Similarity	NPC16435
0.9085	High Similarity	NPC470802
0.9085	High Similarity	NPC162659
0.9085	High Similarity	NPC270456
0.9085	High Similarity	NPC248727
0.9067	High Similarity	NPC59692
0.9067	High Similarity	NPC325860
0.906	High Similarity	NPC195561
0.906	High Similarity	NPC158784
0.9054	High Similarity	NPC473876
0.9054	High Similarity	NPC329836
0.9041	High Similarity	NPC470097
0.9041	High Similarity	NPC63879
0.9041	High Similarity	NPC280092
0.9041	High Similarity	NPC114119
0.9041	High Similarity	NPC45257
0.9041	High Similarity	NPC15659
0.9041	High Similarity	NPC50250
0.9041	High Similarity	NPC93323
0.9041	High Similarity	NPC12641
0.9041	High Similarity	NPC304894
0.9041	High Similarity	NPC471415
0.9028	High Similarity	NPC472090
0.9028	High Similarity	NPC309124
0.9028	High Similarity	NPC259519
0.9028	High Similarity	NPC184797
0.9028	High Similarity	NPC472092
0.9028	High Similarity	NPC472091
0.9026	High Similarity	NPC1253
0.9026	High Similarity	NPC100936
0.9021	High Similarity	NPC211549
0.9014	High Similarity	NPC112246
0.9014	High Similarity	NPC112939
0.9014	High Similarity	NPC470356
0.9014	High Similarity	NPC47398
0.9014	High Similarity	NPC234333
0.9014	High Similarity	NPC61946
0.9014	High Similarity	NPC94750
0.9014	High Similarity	NPC473413
0.9014	High Similarity	NPC474206
0.9014	High Similarity	NPC121812
0.9014	High Similarity	NPC260898
0.9007	High Similarity	NPC470769
0.8986	High Similarity	NPC101376
0.8986	High Similarity	NPC16269
0.8986	High Similarity	NPC21776
0.8986	High Similarity	NPC174251
0.8986	High Similarity	NPC474397
0.8986	High Similarity	NPC153182
0.8973	High Similarity	NPC102044
0.8973	High Similarity	NPC173203
0.8973	High Similarity	NPC47633
0.8973	High Similarity	NPC163508
0.8973	High Similarity	NPC85264
0.8958	High Similarity	NPC127218
0.8958	High Similarity	NPC236306
0.8958	High Similarity	NPC260842
0.8958	High Similarity	NPC245207
0.8958	High Similarity	NPC471388
0.8958	High Similarity	NPC473739
0.8958	High Similarity	NPC232164
0.8958	High Similarity	NPC32630
0.8958	High Similarity	NPC319647
0.8958	High Similarity	NPC25966
0.8951	High Similarity	NPC227503
0.8951	High Similarity	NPC302701
0.8951	High Similarity	NPC269091
0.8951	High Similarity	NPC474639
0.8951	High Similarity	NPC230734
0.8944	High Similarity	NPC256307
0.8944	High Similarity	NPC170694
0.8944	High Similarity	NPC317380
0.8944	High Similarity	NPC478085
0.8944	High Similarity	NPC66840
0.8933	High Similarity	NPC472710
0.8933	High Similarity	NPC472709
0.8926	High Similarity	NPC212142
0.8919	High Similarity	NPC215678
0.8919	High Similarity	NPC126291
0.8919	High Similarity	NPC233980
0.8919	High Similarity	NPC274454
0.8919	High Similarity	NPC150714
0.8919	High Similarity	NPC102280
0.8919	High Similarity	NPC155564
0.8919	High Similarity	NPC95652
0.8919	High Similarity	NPC248053
0.891	High Similarity	NPC12326
0.8904	High Similarity	NPC107161
0.8904	High Similarity	NPC472088
0.8904	High Similarity	NPC472087
0.8897	High Similarity	NPC20520
0.8897	High Similarity	NPC61783
0.8889	High Similarity	NPC276490
0.8889	High Similarity	NPC474282
0.8889	High Similarity	NPC326797
0.8889	High Similarity	NPC477938
0.8889	High Similarity	NPC103976
0.8889	High Similarity	NPC102904
0.8889	High Similarity	NPC107551
0.8889	High Similarity	NPC176051
0.8882	High Similarity	NPC115203
0.8881	High Similarity	NPC151224
0.8881	High Similarity	NPC256262
0.8881	High Similarity	NPC164787

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 NPC477612 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	888
0.2-0.3	1939
0.3-0.4	2705
0.4-0.5	1586
0.5-0.6	888
0.6-0.7	577
0.7-0.8	148
0.8-0.85	5
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8803	High Similarity	NPD1613	Approved
0.8803	High Similarity	NPD1612	Clinical (unspecified phase)
0.8662	High Similarity	NPD4907	Clinical (unspecified phase)
0.8592	High Similarity	NPD3027	Phase 3
0.8521	High Similarity	NPD4908	Phase 1
0.8521	High Similarity	NPD1529	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6166	Phase 2
0.8221	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6674	Discontinued
0.8028	Intermediate Similarity	NPD1610	Phase 2
0.8012	Intermediate Similarity	NPD7228	Approved
0.8012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1934	Approved
0.7917	Intermediate Similarity	NPD7074	Phase 3
0.7905	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD8455	Phase 2
0.7857	Intermediate Similarity	NPD7054	Approved
0.7857	Intermediate Similarity	NPD5844	Phase 1
0.784	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4625	Phase 3
0.7823	Intermediate Similarity	NPD2861	Phase 2
0.7811	Intermediate Similarity	NPD7472	Approved
0.7805	Intermediate Similarity	NPD6234	Discontinued
0.7799	Intermediate Similarity	NPD1653	Approved
0.7791	Intermediate Similarity	NPD8053	Approved
0.7791	Intermediate Similarity	NPD8054	Approved
0.7742	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD37	Approved
0.7711	Intermediate Similarity	NPD6959	Discontinued
0.7711	Intermediate Similarity	NPD7199	Phase 2
0.7683	Intermediate Similarity	NPD4967	Phase 2
0.7683	Intermediate Similarity	NPD4966	Approved
0.7683	Intermediate Similarity	NPD4965	Approved
0.7674	Intermediate Similarity	NPD7808	Phase 3
0.7671	Intermediate Similarity	NPD4749	Approved
0.7622	Intermediate Similarity	NPD1548	Phase 1
0.7619	Intermediate Similarity	NPD8651	Approved
0.7616	Intermediate Similarity	NPD7251	Discontinued
0.761	Intermediate Similarity	NPD7447	Phase 1
0.7593	Intermediate Similarity	NPD4380	Phase 2
0.7584	Intermediate Similarity	NPD3018	Phase 2
0.7576	Intermediate Similarity	NPD7768	Phase 2
0.7566	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3620	Phase 2
0.7566	Intermediate Similarity	NPD4060	Phase 1
0.7561	Intermediate Similarity	NPD2801	Approved
0.7558	Intermediate Similarity	NPD6797	Phase 2
0.7547	Intermediate Similarity	NPD7212	Phase 2
0.7547	Intermediate Similarity	NPD7213	Phase 3
0.7545	Intermediate Similarity	NPD5494	Approved
0.7544	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7473	Discontinued
0.7516	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5124	Phase 1
0.7515	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD7266	Discontinued
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7471	Intermediate Similarity	NPD7549	Discontinued
0.7471	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6232	Discontinued
0.7442	Intermediate Similarity	NPD8156	Discontinued
0.7432	Intermediate Similarity	NPD2983	Phase 2
0.7432	Intermediate Similarity	NPD2982	Phase 2
0.7429	Intermediate Similarity	NPD8312	Approved
0.7429	Intermediate Similarity	NPD8313	Approved
0.7425	Intermediate Similarity	NPD7075	Discontinued
0.7425	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7097	Phase 1
0.7419	Intermediate Similarity	NPD4538	Approved
0.7419	Intermediate Similarity	NPD4536	Approved
0.7416	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8127	Discontinued
0.7394	Intermediate Similarity	NPD5283	Phase 1
0.7391	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD8251	Approved
0.7384	Intermediate Similarity	NPD8252	Approved
0.7384	Intermediate Similarity	NPD8099	Discontinued
0.7371	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2981	Phase 2
0.7365	Intermediate Similarity	NPD3882	Suspended
0.736	Intermediate Similarity	NPD7906	Approved
0.7349	Intermediate Similarity	NPD7819	Suspended
0.7349	Intermediate Similarity	NPD1465	Phase 2
0.7345	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1511	Approved
0.7324	Intermediate Similarity	NPD7843	Approved
0.7321	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6559	Discontinued
0.7312	Intermediate Similarity	NPD7680	Approved
0.7305	Intermediate Similarity	NPD3817	Phase 2
0.7297	Intermediate Similarity	NPD1091	Approved
0.7292	Intermediate Similarity	NPD7157	Approved
0.729	Intermediate Similarity	NPD5735	Approved
0.7284	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5960	Phase 3
0.7261	Intermediate Similarity	NPD5588	Approved
0.7254	Intermediate Similarity	NPD228	Approved
0.7251	Intermediate Similarity	NPD3787	Discontinued
0.725	Intermediate Similarity	NPD7466	Approved
0.7246	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1512	Approved
0.7232	Intermediate Similarity	NPD7310	Approved
0.7232	Intermediate Similarity	NPD7313	Approved
0.7232	Intermediate Similarity	NPD7311	Approved
0.7232	Intermediate Similarity	NPD7312	Approved
0.7229	Intermediate Similarity	NPD7411	Suspended
0.7229	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7041	Phase 2
0.7222	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6099	Approved
0.7215	Intermediate Similarity	NPD6100	Approved
0.7208	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4663	Approved
0.7202	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7309	Approved
0.7189	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1652	Phase 2
0.7188	Intermediate Similarity	NPD5177	Phase 3
0.7178	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6671	Approved
0.717	Intermediate Similarity	NPD5763	Approved
0.717	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5762	Approved
0.7168	Intermediate Similarity	NPD27	Approved
0.7168	Intermediate Similarity	NPD2489	Approved
0.716	Intermediate Similarity	NPD5058	Phase 3
0.7152	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7229	Phase 3
0.7151	Intermediate Similarity	NPD3051	Approved
0.7143	Intermediate Similarity	NPD6331	Phase 2
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4578	Approved
0.7135	Intermediate Similarity	NPD4577	Approved
0.7115	Intermediate Similarity	NPD1558	Phase 1
0.7113	Intermediate Similarity	NPD3022	Approved
0.7113	Intermediate Similarity	NPD3021	Approved
0.711	Intermediate Similarity	NPD2969	Approved
0.711	Intermediate Similarity	NPD2970	Approved
0.7108	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6798	Discontinued
0.7086	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6801	Discontinued
0.7073	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6355	Discontinued
0.7066	Intermediate Similarity	NPD4678	Approved
0.7066	Intermediate Similarity	NPD4675	Approved
0.7063	Intermediate Similarity	NPD3540	Phase 1
0.7063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6584	Phase 3
0.7049	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5846	Approved
0.7047	Intermediate Similarity	NPD6516	Phase 2
0.7042	Intermediate Similarity	NPD2684	Approved
0.7041	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8166	Discontinued
0.7037	Intermediate Similarity	NPD3892	Phase 2
0.7032	Intermediate Similarity	NPD7095	Approved
0.7022	Intermediate Similarity	NPD7685	Pre-registration
0.7019	Intermediate Similarity	NPD2424	Discontinued
0.7019	Intermediate Similarity	NPD1549	Phase 2
0.7018	Intermediate Similarity	NPD7833	Phase 2
0.7018	Intermediate Similarity	NPD7831	Phase 2
0.7018	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4005	Discontinued
0.7	Intermediate Similarity	NPD3539	Phase 1
0.7	Intermediate Similarity	NPD5402	Approved
0.6994	Remote Similarity	NPD6190	Approved
0.6994	Remote Similarity	NPD2677	Approved
0.6989	Remote Similarity	NPD3751	Discontinued
0.6983	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5722	Discontinued
0.6974	Remote Similarity	NPD5327	Phase 3
0.6972	Remote Similarity	NPD290	Approved
0.697	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD422	Phase 1
0.6954	Remote Similarity	NPD3705	Approved
0.6951	Remote Similarity	NPD7124	Phase 2
0.6943	Remote Similarity	NPD6233	Phase 2
0.6933	Remote Similarity	NPD4535	Phase 3
0.6933	Remote Similarity	NPD3750	Approved
0.6928	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6696	Suspended
0.6928	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6072	Discontinued
0.6914	Remote Similarity	NPD7037	Approved
0.6909	Remote Similarity	NPD6143	Clinical (unspecified phase)

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