NPASS Compound

Structure

NPC475492 OpenBabel07101718312D 41 47 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 1.7321 -1.0000 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 -2.5981 -1.5000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 0.5000 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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 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 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 37 1 0 0 0 0 2 38 1 0 0 0 0 3 5 2 0 0 0 0 3 19 1 0 0 0 0 4 10 2 0 0 0 0 4 18 1 0 0 0 0 5 21 1 0 0 0 0 6 8 2 0 0 0 0 6 22 1 0 0 0 0 7 9 2 0 0 0 0 7 23 1 0 0 0 0 8 24 1 0 0 0 0 9 26 1 0 0 0 0 10 27 1 0 0 0 0 11 19 1 0 0 0 0 11 20 1 0 0 0 0 12 18 2 0 0 0 0 12 25 1 0 0 0 0 13 21 2 0 0 0 0 13 28 1 0 0 0 0 14 22 2 0 0 0 0 14 29 1 0 0 0 0 15 23 2 0 0 0 0 15 30 1 0 0 0 0 16 20 1 0 0 0 0 16 39 1 0 0 0 0 17 31 1 0 0 0 0 17 40 1 0 0 0 0 19 28 2 0 0 0 0 20 18 1 6 0 0 0 21 34 1 0 0 0 0 22 35 1 0 0 0 0 23 37 1 0 0 0 0 24 29 2 0 0 0 0 24 32 1 0 0 0 0 25 27 2 0 0 0 0 25 32 1 0 0 0 0 26 30 2 0 0 0 0 26 33 1 0 0 0 0 27 38 1 0 0 0 0 28 39 1 0 0 0 0 29 41 1 0 0 0 0 30 40 1 0 0 0 0 31 33 1 6 0 0 0 31 41 1 0 0 0 0 32 33 1 0 0 0 0 33 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	554.19
Volume:	558.113
LogP:	5.641
LogD:	4.069
LogS:	-4.918
# Rotatable Bonds:	4
TPSA:	106.84
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.323
Synthetic Accessibility Score:	4.296
Fsp3:	0.273
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.524
MDCK Permeability:	1.4865391676721629e-05
Pgp-inhibitor:	0.035
Pgp-substrate:	0.399
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.399

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	99.63002014160156%
Volume Distribution (VD):	0.551
Pgp-substrate:	0.956965446472168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.159
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.46
CYP2C9-inhibitor:	0.87
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.418
CYP2D6-substrate:	0.958
CYP3A4-inhibitor:	0.866
CYP3A4-substrate:	0.915

ADMET: Excretion

Clearance (CL):	9.247
Half-life (T1/2):	0.079

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.555
Drug-inuced Liver Injury (DILI):	0.805
AMES Toxicity:	0.746
Rat Oral Acute Toxicity:	0.828
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.497
Carcinogencity:	0.146
Eye Corrosion:	0.003
Eye Irritation:	0.66
Respiratory Toxicity:	0.232

Download Data

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

Natural Product: NPC475492

Natural Product ID:	NPC475492
*Common Name:**	Gliricidin
IUPAC Name:	(6aR,12aR)-12-[5-[(3R)-7-hydroxy-3,4-dihydro-2H-chromen-3-yl]-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6H-chromeno[2,3-c]chromene-9,12a-diol
Synonyms:	Gliricidin
Standard InCHIKey:	AAYNXSSLTTZFMB-PUVHLHJNSA-N
Standard InCHI:	InChI=1S/C33H30O8/c1-37-23-7-9-26-30(15-23)40-17-31-33(26,36)32(24-8-6-22(35)14-29(24)41-31)25-12-18(4-10-27(25)38-2)20-11-19-3-5-21(34)13-28(19)39-16-20/h3-10,12-15,20,31-32,34-36H,11,16-17H2,1-2H3/t20-,31+,32?,33+/m0/s1
SMILES:	COC1=CC2=C(C=C1)C3(C(CO2)OC4=C(C3C5=C(C=CC(=C5)C6CC7=C(C=C(C=C7)O)OC6)OC)C=CC(=C4)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506629
PubChem CID:	10554770
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids

*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
NPO14052	Gliricidia sepium	Species	Fabaceae	Eukaryota	bark	n.a.	n.a.	PMID[9917318]
NPO14052	Gliricidia sepium	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	243.7	ug.mL-1	PMID[504429]

☑ 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 NPC475492 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	450
0.1-0.2	1497
0.2-0.3	3893
0.3-0.4	10625
0.4-0.5	8141
0.5-0.6	4300
0.6-0.7	7314
0.7-0.8	5349
0.8-0.85	697
0.85-0.9	330
0.9-0.95	95
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9635	High Similarity	NPC100482
0.9635	High Similarity	NPC277331
0.9433	High Similarity	NPC102280
0.9433	High Similarity	NPC248053
0.9433	High Similarity	NPC155564
0.9416	High Similarity	NPC470307
0.9416	High Similarity	NPC470308
0.9343	High Similarity	NPC471522
0.9338	High Similarity	NPC476615
0.9338	High Similarity	NPC476616
0.9338	High Similarity	NPC476617
0.9241	High Similarity	NPC471403
0.9241	High Similarity	NPC259707
0.9236	High Similarity	NPC211561
0.9231	High Similarity	NPC263940
0.9231	High Similarity	NPC262911
0.9231	High Similarity	NPC294558
0.9231	High Similarity	NPC236202
0.9231	High Similarity	NPC170103
0.9231	High Similarity	NPC70409
0.9231	High Similarity	NPC204770
0.9231	High Similarity	NPC108811
0.9231	High Similarity	NPC202742
0.9231	High Similarity	NPC18185
0.9231	High Similarity	NPC58190
0.9231	High Similarity	NPC82917
0.9209	High Similarity	NPC475836
0.9178	High Similarity	NPC226809
0.9178	High Similarity	NPC279406
0.9172	High Similarity	NPC477612
0.9161	High Similarity	NPC96576
0.9124	High Similarity	NPC92805
0.9116	High Similarity	NPC224161
0.9065	High Similarity	NPC20829
0.9065	High Similarity	NPC262585
0.9065	High Similarity	NPC18189
0.9058	High Similarity	NPC124085
0.9058	High Similarity	NPC117048
0.9054	High Similarity	NPC46335
0.9048	High Similarity	NPC322899
0.9048	High Similarity	NPC46283
0.9048	High Similarity	NPC226108
0.9048	High Similarity	NPC272552
0.9048	High Similarity	NPC44192
0.9048	High Similarity	NPC134911
0.9048	High Similarity	NPC469944
0.9034	High Similarity	NPC227516
0.9034	High Similarity	NPC20757
0.9	High Similarity	NPC474687
0.8986	High Similarity	NPC77196
0.8986	High Similarity	NPC85435
0.8978	High Similarity	NPC293203
0.8978	High Similarity	NPC118683
0.8978	High Similarity	NPC68205
0.8978	High Similarity	NPC244888
0.8978	High Similarity	NPC103799
0.8978	High Similarity	NPC164804
0.8978	High Similarity	NPC211413
0.8966	High Similarity	NPC153182
0.8966	High Similarity	NPC174251
0.8929	High Similarity	NPC3049
0.8921	High Similarity	NPC198154
0.8921	High Similarity	NPC115335
0.8921	High Similarity	NPC225696
0.8921	High Similarity	NPC97834
0.8921	High Similarity	NPC223008
0.8921	High Similarity	NPC296915
0.8919	High Similarity	NPC59692
0.8913	High Similarity	NPC13005
0.8904	High Similarity	NPC281549
0.8897	High Similarity	NPC222572
0.8897	High Similarity	NPC53986
0.8897	High Similarity	NPC38664
0.8897	High Similarity	NPC87224
0.8897	High Similarity	NPC274454
0.8897	High Similarity	NPC215678
0.8889	High Similarity	NPC171932
0.8889	High Similarity	NPC28440
0.8874	High Similarity	NPC4809
0.8874	High Similarity	NPC147743
0.8874	High Similarity	NPC73517
0.8859	High Similarity	NPC306267
0.8859	High Similarity	NPC20050
0.8857	High Similarity	NPC125579
0.8844	High Similarity	NPC321657
0.8844	High Similarity	NPC318373
0.8841	High Similarity	NPC129784
0.8841	High Similarity	NPC162801
0.8841	High Similarity	NPC236014
0.8841	High Similarity	NPC164574
0.8841	High Similarity	NPC300875
0.8841	High Similarity	NPC12875
0.8841	High Similarity	NPC196765
0.8841	High Similarity	NPC228369
0.8841	High Similarity	NPC118114
0.8841	High Similarity	NPC206224
0.8841	High Similarity	NPC476166
0.8841	High Similarity	NPC17343
0.8841	High Similarity	NPC207892
0.8841	High Similarity	NPC129106
0.8841	High Similarity	NPC268917
0.8841	High Similarity	NPC280653
0.8841	High Similarity	NPC150011
0.8832	High Similarity	NPC93962
0.8816	High Similarity	NPC159526
0.8816	High Similarity	NPC106601
0.8816	High Similarity	NPC212614
0.8816	High Similarity	NPC471404
0.8816	High Similarity	NPC205613
0.8816	High Similarity	NPC151474
0.8816	High Similarity	NPC86630
0.8816	High Similarity	NPC185231
0.8811	High Similarity	NPC178054
0.8786	High Similarity	NPC473107
0.8768	High Similarity	NPC470225
0.8768	High Similarity	NPC27187
0.8767	High Similarity	NPC14468
0.8759	High Similarity	NPC473108
0.8759	High Similarity	NPC225445
0.8759	High Similarity	NPC274717
0.875	High Similarity	NPC2613
0.875	High Similarity	NPC283049
0.875	High Similarity	NPC50315
0.875	High Similarity	NPC59841
0.875	High Similarity	NPC230479
0.875	High Similarity	NPC204347
0.875	High Similarity	NPC475891
0.875	High Similarity	NPC26879
0.8741	High Similarity	NPC22317
0.8741	High Similarity	NPC262189
0.8716	High Similarity	NPC476969
0.8705	High Similarity	NPC181497
0.8705	High Similarity	NPC271945
0.8699	High Similarity	NPC181615
0.8696	High Similarity	NPC134360
0.869	High Similarity	NPC116922
0.8686	High Similarity	NPC149796
0.8676	High Similarity	NPC103420
0.8676	High Similarity	NPC17809
0.8676	High Similarity	NPC188022
0.8676	High Similarity	NPC102540
0.8676	High Similarity	NPC285040
0.8675	High Similarity	NPC157333
0.8671	High Similarity	NPC260741
0.8671	High Similarity	NPC70682
0.8667	High Similarity	NPC233467
0.8667	High Similarity	NPC325860
0.8662	High Similarity	NPC141717
0.8658	High Similarity	NPC162976
0.8658	High Similarity	NPC118000
0.8658	High Similarity	NPC205501
0.8652	High Similarity	NPC184269
0.8645	High Similarity	NPC12326
0.8639	High Similarity	NPC260397
0.863	High Similarity	NPC304894
0.863	High Similarity	NPC15659
0.863	High Similarity	NPC177597
0.8623	High Similarity	NPC39064
0.8623	High Similarity	NPC471064
0.8623	High Similarity	NPC47283
0.8621	High Similarity	NPC186033
0.8621	High Similarity	NPC472353
0.8621	High Similarity	NPC84207
0.8621	High Similarity	NPC5253
0.8621	High Similarity	NPC139976
0.8621	High Similarity	NPC128337
0.8621	High Similarity	NPC230718
0.8621	High Similarity	NPC49542
0.8613	High Similarity	NPC276212
0.8603	High Similarity	NPC246648
0.8603	High Similarity	NPC197351
0.8603	High Similarity	NPC106914
0.8603	High Similarity	NPC134195
0.8603	High Similarity	NPC86502
0.8601	High Similarity	NPC211549
0.8601	High Similarity	NPC262328
0.8601	High Similarity	NPC87777
0.86	High Similarity	NPC321972
0.86	High Similarity	NPC302915
0.86	High Similarity	NPC329343
0.86	High Similarity	NPC324517
0.8592	High Similarity	NPC151224
0.8592	High Similarity	NPC15109
0.8592	High Similarity	NPC11727
0.8592	High Similarity	NPC473413
0.8581	High Similarity	NPC6702
0.8581	High Similarity	NPC16269
0.8581	High Similarity	NPC112819
0.8581	High Similarity	NPC133209
0.8581	High Similarity	NPC474397
0.8581	High Similarity	NPC111134
0.8581	High Similarity	NPC21776
0.8581	High Similarity	NPC101376
0.8571	High Similarity	NPC469557
0.8571	High Similarity	NPC469701
0.8562	High Similarity	NPC173203
0.8562	High Similarity	NPC163508
0.8552	High Similarity	NPC35216
0.8552	High Similarity	NPC5155
0.8552	High Similarity	NPC108674

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 NPC475492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	854
0.2-0.3	1779
0.3-0.4	2674
0.4-0.5	1722
0.5-0.6	1002
0.6-0.7	613
0.7-0.8	116
0.8-0.85	9
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9044	High Similarity	NPD4907	Clinical (unspecified phase)
0.8897	High Similarity	NPD4908	Phase 1
0.8382	Intermediate Similarity	NPD1610	Phase 2
0.8252	Intermediate Similarity	NPD1613	Approved
0.8252	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD8455	Phase 2
0.8042	Intermediate Similarity	NPD4625	Phase 3
0.8028	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD1548	Phase 1
0.7917	Intermediate Similarity	NPD3027	Phase 3
0.7902	Intermediate Similarity	NPD2861	Phase 2
0.7888	Intermediate Similarity	NPD6959	Discontinued
0.7872	Intermediate Similarity	NPD4749	Approved
0.7862	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7212	Phase 2
0.7843	Intermediate Similarity	NPD7213	Phase 3
0.7823	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD5124	Phase 1
0.7792	Intermediate Similarity	NPD7447	Phase 1
0.7771	Intermediate Similarity	NPD4380	Phase 2
0.775	Intermediate Similarity	NPD7768	Phase 2
0.7744	Intermediate Similarity	NPD6166	Phase 2
0.7744	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD7097	Phase 1
0.7711	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8651	Approved
0.764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4060	Phase 1
0.7625	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4536	Approved
0.76	Intermediate Similarity	NPD4538	Approved
0.76	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7075	Discontinued
0.7564	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7466	Approved
0.75	Intermediate Similarity	NPD7411	Suspended
0.7485	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1091	Approved
0.7468	Intermediate Similarity	NPD6674	Discontinued
0.7456	Intermediate Similarity	NPD7074	Phase 3
0.7453	Intermediate Similarity	NPD1934	Approved
0.7452	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7228	Approved
0.7436	Intermediate Similarity	NPD5058	Phase 3
0.7434	Intermediate Similarity	NPD5588	Approved
0.7434	Intermediate Similarity	NPD5960	Phase 3
0.7407	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5844	Phase 1
0.7391	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7843	Approved
0.7384	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD8312	Approved
0.7383	Intermediate Similarity	NPD6798	Discontinued
0.7383	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD7157	Approved
0.7355	Intermediate Similarity	NPD1652	Phase 2
0.7341	Intermediate Similarity	NPD8053	Approved
0.7341	Intermediate Similarity	NPD8054	Approved
0.7338	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6234	Discontinued
0.7301	Intermediate Similarity	NPD7819	Suspended
0.7294	Intermediate Similarity	NPD7054	Approved
0.729	Intermediate Similarity	NPD1549	Phase 2
0.729	Intermediate Similarity	NPD2424	Discontinued
0.7289	Intermediate Similarity	NPD5494	Approved
0.7273	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD6099	Approved
0.7267	Intermediate Similarity	NPD6559	Discontinued
0.726	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7472	Approved
0.7246	Intermediate Similarity	NPD7199	Phase 2
0.7241	Intermediate Similarity	NPD422	Phase 1
0.7239	Intermediate Similarity	NPD37	Approved
0.7239	Intermediate Similarity	NPD6801	Discontinued
0.7237	Intermediate Similarity	NPD6355	Discontinued
0.7234	Intermediate Similarity	NPD6671	Approved
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2684	Approved
0.7225	Intermediate Similarity	NPD7549	Discontinued
0.7225	Intermediate Similarity	NPD7808	Phase 3
0.7222	Intermediate Similarity	NPD5846	Approved
0.7222	Intermediate Similarity	NPD6516	Phase 2
0.7219	Intermediate Similarity	NPD6233	Phase 2
0.7212	Intermediate Similarity	NPD4966	Approved
0.7212	Intermediate Similarity	NPD4967	Phase 2
0.7212	Intermediate Similarity	NPD4965	Approved
0.7209	Intermediate Similarity	NPD6797	Phase 2
0.7205	Intermediate Similarity	NPD1653	Approved
0.7202	Intermediate Similarity	NPD3787	Discontinued
0.7197	Intermediate Similarity	NPD3750	Approved
0.7197	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3018	Phase 2
0.7178	Intermediate Similarity	NPD6072	Discontinued
0.7171	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7041	Phase 2
0.717	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7251	Discontinued
0.716	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD290	Approved
0.7143	Intermediate Similarity	NPD6583	Phase 3
0.7143	Intermediate Similarity	NPD6582	Phase 2
0.7134	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5735	Approved
0.7114	Intermediate Similarity	NPD6584	Phase 3
0.7101	Intermediate Similarity	NPD7229	Phase 3
0.7101	Intermediate Similarity	NPD6232	Discontinued
0.7093	Intermediate Similarity	NPD8156	Discontinued
0.7091	Intermediate Similarity	NPD2801	Approved
0.7089	Intermediate Similarity	NPD4535	Phase 3
0.7086	Intermediate Similarity	NPD7095	Approved
0.7076	Intermediate Similarity	NPD7473	Discontinued
0.7069	Intermediate Similarity	NPD7240	Approved
0.7066	Intermediate Similarity	NPD3749	Approved
0.7051	Intermediate Similarity	NPD2796	Approved
0.7037	Intermediate Similarity	NPD5403	Approved
0.7035	Intermediate Similarity	NPD8099	Discontinued
0.7035	Intermediate Similarity	NPD8251	Approved
0.7035	Intermediate Similarity	NPD8252	Approved
0.7029	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2982	Phase 2
0.7027	Intermediate Similarity	NPD2983	Phase 2
0.7019	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7266	Discontinued
0.7006	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD7030	Discontinued
0.7006	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD3122	Phase 3
0.7	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1465	Phase 2
0.6987	Remote Similarity	NPD1510	Phase 2
0.6987	Remote Similarity	NPD7033	Discontinued
0.6981	Remote Similarity	NPD3892	Phase 2
0.6981	Remote Similarity	NPD4628	Phase 3
0.698	Remote Similarity	NPD6696	Suspended
0.6972	Remote Similarity	NPD5283	Phase 1
0.6966	Remote Similarity	NPD7741	Discontinued
0.6964	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7037	Approved
0.6959	Remote Similarity	NPD2981	Phase 2
0.6957	Remote Similarity	NPD6799	Approved
0.6957	Remote Similarity	NPD1511	Approved
0.6957	Remote Similarity	NPD968	Approved
0.6951	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2238	Phase 2
0.6948	Remote Similarity	NPD3620	Phase 2
0.6946	Remote Similarity	NPD5402	Approved
0.6946	Remote Similarity	NPD3817	Phase 2
0.6936	Remote Similarity	NPD3751	Discontinued
0.6936	Remote Similarity	NPD3818	Discontinued
0.6933	Remote Similarity	NPD2797	Approved
0.6927	Remote Similarity	NPD7906	Approved
0.6923	Remote Similarity	NPD2200	Suspended
0.6914	Remote Similarity	NPD5401	Approved
0.6913	Remote Similarity	NPD5327	Phase 3
0.6912	Remote Similarity	NPD940	Approved
0.6912	Remote Similarity	NPD846	Approved
0.691	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6599	Discontinued
0.6905	Remote Similarity	NPD7773	Phase 2
0.6905	Remote Similarity	NPD3882	Suspended
0.6901	Remote Similarity	NPD5535	Approved
0.6899	Remote Similarity	NPD6004	Phase 3
0.6899	Remote Similarity	NPD6005	Phase 3
0.6899	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6002	Phase 3
0.6894	Remote Similarity	NPD6666	Approved
0.6894	Remote Similarity	NPD6667	Approved
0.6889	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5929	Approved
0.6879	Remote Similarity	NPD3748	Approved
0.6879	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7003	Approved
0.6871	Remote Similarity	NPD5126	Approved
0.6871	Remote Similarity	NPD1512	Approved
0.6871	Remote Similarity	NPD5125	Phase 3
0.6859	Remote Similarity	NPD6353	Approved
0.6859	Remote Similarity	NPD4097	Suspended
0.6852	Remote Similarity	NPD7390	Discontinued
0.6848	Remote Similarity	NPD7458	Discontinued
0.6842	Remote Similarity	NPD8127	Discontinued
0.6839	Remote Similarity	NPD4140	Approved
0.6839	Remote Similarity	NPD1240	Approved
0.6836	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2677	Approved
0.6828	Remote Similarity	NPD7340	Approved
0.6826	Remote Similarity	NPD4433	Discontinued
0.6823	Remote Similarity	NPD7783	Phase 2

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