NPASS Compound

Structure

CID78527 OpenBabel06191715412D 33 33 0 0 1 0 0 0 0 0999 V2000 -5.5755 7.0379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1272 8.7110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4530 5.0367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6766 2.1390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 -1.1088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6437 6.5203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8672 3.6225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0908 0.7247 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 -3.9025 7.4862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6778 6.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1260 4.5884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9013 3.3637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3496 1.6907 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1248 0.4659 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 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8684 7.7450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4189 5.2956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6425 2.3978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -0.8660 -1.5000 0.0000 C 0 0 2 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 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 29 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 11 21 1 0 0 0 0 12 23 2 0 0 0 0 13 24 1 0 0 0 0 14 24 2 0 0 0 0 15 25 1 0 0 0 0 16 25 2 0 0 0 0 17 28 1 0 0 0 0 18 20 1 0 0 0 0 18 27 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 22 26 1 0 0 0 0 22 32 2 0 0 0 0 26 27 2 0 0 0 0 27 28 1 0 0 0 0 28 29 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 30 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	532.068
LogP:	6.894
LogD:	4.923
LogS:	-4.589
# Rotatable Bonds:	13
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.169
Synthetic Accessibility Score:	4.561
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.697
MDCK Permeability:	2.238553497591056e-05
Pgp-inhibitor:	0.91
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.792
30% Bioavailability (F30%):	0.066

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.439
Plasma Protein Binding (PPB):	97.47980499267578%
Volume Distribution (VD):	1.807
Pgp-substrate:	3.0283989906311035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.13
CYP2C19-inhibitor:	0.194
CYP2C19-substrate:	0.764
CYP2C9-inhibitor:	0.414
CYP2C9-substrate:	0.374
CYP2D6-inhibitor:	0.658
CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.354

ADMET: Excretion

Clearance (CL):	7.044
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.734
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.745
Skin Sensitization:	0.927
Carcinogencity:	0.045
Eye Corrosion:	0.031
Eye Irritation:	0.101
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC78527

Natural Product ID:	NPC78527
*Common Name:**	Iridal
IUPAC Name:	(2Z)-2-[(2R,3S,4S)-4-hydroxy-2-(3-hydroxypropyl)-3,4-dimethyl-3-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]cyclohexylidene]propanal
Synonyms:	Iridal
Standard InCHIKey:	KWHXMASXPBOSRE-JKIIOOKNSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-23(2)12-8-13-24(3)14-9-15-25(4)16-10-19-29(6)28(17-11-21-31)27(26(5)22-32)18-20-30(29,7)33/h12,14,16,22,28,31,33H,8-11,13,15,17-21H2,1-7H3/b24-14+,25-16+,27-26-/t28-,29+,30+/m1/s1
SMILES:	OCCC[C@@H]1/C(=C(C=O)/C)/CC[C@]([C@@]1(C)CC/C=C(/CC/C=C(/CCC=C(C)C)C)C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1173373
PubChem CID:	5318463
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21465599]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[22388969]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25036154]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25204177]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31246464]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7528	Belamcanda chinensis	Species	Iridaceae	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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.8	ug.mL-1	PMID[451696]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	26.0	ug.mL-1	PMID[451696]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	14.0	ug.mL-1	PMID[451696]

☑ 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 NPC78527 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	154
0.1-0.2	1162
0.2-0.3	6219
0.3-0.4	16283
0.4-0.5	8196
0.5-0.6	6582
0.6-0.7	3493
0.7-0.8	582
0.8-0.85	20
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9041	High Similarity	NPC470428
0.8919	High Similarity	NPC476949
0.88	High Similarity	NPC470429
0.8649	High Similarity	NPC167873
0.8649	High Similarity	NPC1973
0.8608	High Similarity	NPC280203
0.8406	Intermediate Similarity	NPC225415
0.8356	Intermediate Similarity	NPC167706
0.8228	Intermediate Similarity	NPC2524
0.8205	Intermediate Similarity	NPC281880
0.8193	Intermediate Similarity	NPC257485
0.8182	Intermediate Similarity	NPC80088
0.8182	Intermediate Similarity	NPC253561
0.8171	Intermediate Similarity	NPC475772
0.8171	Intermediate Similarity	NPC89747
0.8158	Intermediate Similarity	NPC250621
0.8133	Intermediate Similarity	NPC476366
0.8133	Intermediate Similarity	NPC201048
0.8101	Intermediate Similarity	NPC159148
0.8077	Intermediate Similarity	NPC283789
0.8072	Intermediate Similarity	NPC206060
0.8052	Intermediate Similarity	NPC132542
0.8052	Intermediate Similarity	NPC197659
0.8026	Intermediate Similarity	NPC32832
0.8025	Intermediate Similarity	NPC470812
0.7976	Intermediate Similarity	NPC472983
0.7975	Intermediate Similarity	NPC472301
0.7975	Intermediate Similarity	NPC2482
0.7949	Intermediate Similarity	NPC59436
0.7927	Intermediate Similarity	NPC79573
0.7927	Intermediate Similarity	NPC470574
0.7922	Intermediate Similarity	NPC470749
0.7922	Intermediate Similarity	NPC265588
0.7922	Intermediate Similarity	NPC263582
0.7901	Intermediate Similarity	NPC64600
0.7901	Intermediate Similarity	NPC476927
0.7901	Intermediate Similarity	NPC307258
0.7895	Intermediate Similarity	NPC22134
0.7895	Intermediate Similarity	NPC91858
0.7895	Intermediate Similarity	NPC477138
0.7895	Intermediate Similarity	NPC243342
0.7882	Intermediate Similarity	NPC191684
0.7875	Intermediate Similarity	NPC473217
0.7875	Intermediate Similarity	NPC119229
0.7875	Intermediate Similarity	NPC90055
0.7867	Intermediate Similarity	NPC242001
0.7867	Intermediate Similarity	NPC164022
0.7857	Intermediate Similarity	NPC474925
0.7857	Intermediate Similarity	NPC473229
0.7848	Intermediate Similarity	NPC308038
0.7848	Intermediate Similarity	NPC229204
0.7831	Intermediate Similarity	NPC175145
0.7831	Intermediate Similarity	NPC94755
0.7831	Intermediate Similarity	NPC235341
0.7831	Intermediate Similarity	NPC477579
0.7831	Intermediate Similarity	NPC95594
0.7831	Intermediate Similarity	NPC475069
0.7821	Intermediate Similarity	NPC283619
0.7821	Intermediate Similarity	NPC470758
0.7821	Intermediate Similarity	NPC470711
0.7821	Intermediate Similarity	NPC85105
0.7821	Intermediate Similarity	NPC219809
0.7821	Intermediate Similarity	NPC149550
0.7808	Intermediate Similarity	NPC68703
0.7808	Intermediate Similarity	NPC69649
0.7805	Intermediate Similarity	NPC476412
0.7792	Intermediate Similarity	NPC477923
0.7792	Intermediate Similarity	NPC66566
0.7792	Intermediate Similarity	NPC291503
0.7792	Intermediate Similarity	NPC114236
0.7778	Intermediate Similarity	NPC48362
0.7765	Intermediate Similarity	NPC472973
0.7763	Intermediate Similarity	NPC182717
0.7763	Intermediate Similarity	NPC68443
0.775	Intermediate Similarity	NPC471514
0.775	Intermediate Similarity	NPC172013
0.7738	Intermediate Similarity	NPC141292
0.7733	Intermediate Similarity	NPC92801
0.7733	Intermediate Similarity	NPC34834
0.7733	Intermediate Similarity	NPC145498
0.7727	Intermediate Similarity	NPC13924
0.7722	Intermediate Similarity	NPC285761
0.7722	Intermediate Similarity	NPC471409
0.7722	Intermediate Similarity	NPC297996
0.7722	Intermediate Similarity	NPC62336
0.7722	Intermediate Similarity	NPC275494
0.7711	Intermediate Similarity	NPC109528
0.7703	Intermediate Similarity	NPC94192
0.7703	Intermediate Similarity	NPC208999
0.7692	Intermediate Similarity	NPC470525
0.7683	Intermediate Similarity	NPC470165
0.7683	Intermediate Similarity	NPC79945
0.7674	Intermediate Similarity	NPC183283
0.7671	Intermediate Similarity	NPC476406
0.7671	Intermediate Similarity	NPC149680
0.7662	Intermediate Similarity	NPC100334
0.7662	Intermediate Similarity	NPC306727
0.7654	Intermediate Similarity	NPC473420
0.7654	Intermediate Similarity	NPC170303
0.7654	Intermediate Similarity	NPC121984
0.7654	Intermediate Similarity	NPC142163
0.7647	Intermediate Similarity	NPC472802
0.7647	Intermediate Similarity	NPC471722
0.7647	Intermediate Similarity	NPC292491
0.7647	Intermediate Similarity	NPC310752
0.7647	Intermediate Similarity	NPC104560
0.7647	Intermediate Similarity	NPC291665
0.7639	Intermediate Similarity	NPC290367
0.7639	Intermediate Similarity	NPC101128
0.7632	Intermediate Similarity	NPC471272
0.7632	Intermediate Similarity	NPC477792
0.7632	Intermediate Similarity	NPC110799
0.7625	Intermediate Similarity	NPC170394
0.7625	Intermediate Similarity	NPC80530
0.7625	Intermediate Similarity	NPC100906
0.7625	Intermediate Similarity	NPC291379
0.7625	Intermediate Similarity	NPC152061
0.7625	Intermediate Similarity	NPC273410
0.7619	Intermediate Similarity	NPC179591
0.7619	Intermediate Similarity	NPC73038
0.7619	Intermediate Similarity	NPC158393
0.7619	Intermediate Similarity	NPC72133
0.7619	Intermediate Similarity	NPC472985
0.7619	Intermediate Similarity	NPC472974
0.7619	Intermediate Similarity	NPC472986
0.7606	Intermediate Similarity	NPC475251
0.76	Intermediate Similarity	NPC9942
0.76	Intermediate Similarity	NPC476431
0.7595	Intermediate Similarity	NPC157996
0.7595	Intermediate Similarity	NPC203403
0.7595	Intermediate Similarity	NPC477924
0.7595	Intermediate Similarity	NPC471798
0.7595	Intermediate Similarity	NPC91594
0.7595	Intermediate Similarity	NPC90979
0.7595	Intermediate Similarity	NPC130136
0.7595	Intermediate Similarity	NPC325946
0.7595	Intermediate Similarity	NPC266193
0.7595	Intermediate Similarity	NPC40394
0.7595	Intermediate Similarity	NPC472805
0.7595	Intermediate Similarity	NPC101475
0.7595	Intermediate Similarity	NPC34177
0.7595	Intermediate Similarity	NPC257666
0.7595	Intermediate Similarity	NPC214570
0.759	Intermediate Similarity	NPC306951
0.759	Intermediate Similarity	NPC85774
0.759	Intermediate Similarity	NPC33913
0.759	Intermediate Similarity	NPC214043
0.759	Intermediate Similarity	NPC472265
0.759	Intermediate Similarity	NPC473246
0.759	Intermediate Similarity	NPC251170
0.7586	Intermediate Similarity	NPC472975
0.7586	Intermediate Similarity	NPC472978
0.7568	Intermediate Similarity	NPC197805
0.7568	Intermediate Similarity	NPC263161
0.7568	Intermediate Similarity	NPC96962
0.7561	Intermediate Similarity	NPC92226
0.7561	Intermediate Similarity	NPC93590
0.7561	Intermediate Similarity	NPC103486
0.7561	Intermediate Similarity	NPC470813
0.7561	Intermediate Similarity	NPC256112
0.7558	Intermediate Similarity	NPC472240
0.7558	Intermediate Similarity	NPC86319
0.7558	Intermediate Similarity	NPC314727
0.7558	Intermediate Similarity	NPC184663
0.7558	Intermediate Similarity	NPC275740
0.7558	Intermediate Similarity	NPC262858
0.7534	Intermediate Similarity	NPC258595
0.7532	Intermediate Similarity	NPC471799
0.7532	Intermediate Similarity	NPC474140
0.7531	Intermediate Similarity	NPC236237
0.7531	Intermediate Similarity	NPC102253
0.7531	Intermediate Similarity	NPC104120
0.7531	Intermediate Similarity	NPC322313
0.7531	Intermediate Similarity	NPC148685
0.7531	Intermediate Similarity	NPC157895
0.7531	Intermediate Similarity	NPC306095
0.7531	Intermediate Similarity	NPC476809
0.7531	Intermediate Similarity	NPC13554
0.7529	Intermediate Similarity	NPC475740
0.75	Intermediate Similarity	NPC196753
0.75	Intermediate Similarity	NPC253807
0.75	Intermediate Similarity	NPC230295
0.75	Intermediate Similarity	NPC300499
0.75	Intermediate Similarity	NPC133954
0.75	Intermediate Similarity	NPC6978
0.75	Intermediate Similarity	NPC99168
0.75	Intermediate Similarity	NPC158662
0.75	Intermediate Similarity	NPC70685
0.75	Intermediate Similarity	NPC98386
0.75	Intermediate Similarity	NPC167037
0.75	Intermediate Similarity	NPC22955
0.75	Intermediate Similarity	NPC239098
0.75	Intermediate Similarity	NPC474989
0.75	Intermediate Similarity	NPC470396
0.75	Intermediate Similarity	NPC469948
0.75	Intermediate Similarity	NPC138621
0.75	Intermediate Similarity	NPC22133
0.75	Intermediate Similarity	NPC475994
0.75	Intermediate Similarity	NPC321514
0.75	Intermediate Similarity	NPC275910

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 NPC78527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1756
0.2-0.3	4191
0.3-0.4	2227
0.4-0.5	440
0.5-0.6	219
0.6-0.7	167
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7619	Intermediate Similarity	NPD3618	Phase 1
0.7558	Intermediate Similarity	NPD5328	Approved
0.7531	Intermediate Similarity	NPD7525	Registered
0.7436	Intermediate Similarity	NPD6924	Approved
0.7436	Intermediate Similarity	NPD6926	Approved
0.7407	Intermediate Similarity	NPD7645	Phase 2
0.7386	Intermediate Similarity	NPD7515	Phase 2
0.7386	Intermediate Similarity	NPD6079	Approved
0.7381	Intermediate Similarity	NPD3666	Approved
0.7381	Intermediate Similarity	NPD3133	Approved
0.7381	Intermediate Similarity	NPD3665	Phase 1
0.7303	Intermediate Similarity	NPD4202	Approved
0.7253	Intermediate Similarity	NPD4697	Phase 3
0.725	Intermediate Similarity	NPD6933	Approved
0.7209	Intermediate Similarity	NPD5279	Phase 3
0.7195	Intermediate Similarity	NPD4195	Approved
0.7176	Intermediate Similarity	NPD4786	Approved
0.7159	Intermediate Similarity	NPD4753	Phase 2
0.7143	Intermediate Similarity	NPD3667	Approved
0.7143	Intermediate Similarity	NPD4223	Phase 3
0.7143	Intermediate Similarity	NPD4221	Approved
0.7125	Intermediate Similarity	NPD7339	Approved
0.7125	Intermediate Similarity	NPD6942	Approved
0.7108	Intermediate Similarity	NPD7509	Discontinued
0.7108	Intermediate Similarity	NPD4695	Discontinued
0.7093	Intermediate Similarity	NPD5329	Approved
0.7037	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7748	Approved
0.7011	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4755	Approved
0.6977	Remote Similarity	NPD4197	Approved
0.6974	Remote Similarity	NPD7331	Phase 2
0.6962	Remote Similarity	NPD4243	Approved
0.6923	Remote Similarity	NPD6923	Approved
0.6923	Remote Similarity	NPD6922	Approved
0.6915	Remote Similarity	NPD7638	Approved
0.6914	Remote Similarity	NPD8264	Approved
0.6905	Remote Similarity	NPD6931	Approved
0.6905	Remote Similarity	NPD6930	Phase 2
0.6882	Remote Similarity	NPD5222	Approved
0.6882	Remote Similarity	NPD5221	Approved
0.6882	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4788	Approved
0.6842	Remote Similarity	NPD5286	Approved
0.6842	Remote Similarity	NPD7639	Approved
0.6842	Remote Similarity	NPD4700	Approved
0.6842	Remote Similarity	NPD4696	Approved
0.6842	Remote Similarity	NPD7341	Phase 2
0.6842	Remote Similarity	NPD5285	Approved
0.6842	Remote Similarity	NPD7640	Approved
0.6835	Remote Similarity	NPD7144	Approved
0.6835	Remote Similarity	NPD7143	Approved
0.6818	Remote Similarity	NPD4690	Approved
0.6818	Remote Similarity	NPD4688	Approved
0.6818	Remote Similarity	NPD5690	Phase 2
0.6818	Remote Similarity	NPD4693	Phase 3
0.6818	Remote Similarity	NPD4689	Approved
0.6818	Remote Similarity	NPD4694	Approved
0.6818	Remote Similarity	NPD4623	Approved
0.6818	Remote Similarity	NPD4138	Approved
0.6818	Remote Similarity	NPD4519	Discontinued
0.6818	Remote Similarity	NPD5280	Approved
0.6818	Remote Similarity	NPD5205	Approved
0.6809	Remote Similarity	NPD5173	Approved
0.6809	Remote Similarity	NPD6084	Phase 2
0.6809	Remote Similarity	NPD7902	Approved
0.6809	Remote Similarity	NPD6083	Phase 2
0.679	Remote Similarity	NPD4784	Approved
0.679	Remote Similarity	NPD4785	Approved
0.6786	Remote Similarity	NPD6929	Approved
0.6774	Remote Similarity	NPD4629	Approved
0.6774	Remote Similarity	NPD5210	Approved
0.6771	Remote Similarity	NPD5223	Approved
0.675	Remote Similarity	NPD7151	Approved
0.675	Remote Similarity	NPD7152	Approved
0.675	Remote Similarity	NPD7150	Approved
0.6747	Remote Similarity	NPD6932	Approved
0.6737	Remote Similarity	NPD4225	Approved
0.6706	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1696	Phase 3
0.6705	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4633	Approved
0.6701	Remote Similarity	NPD5224	Approved
0.6701	Remote Similarity	NPD5211	Phase 2
0.6701	Remote Similarity	NPD5226	Approved
0.6701	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD368	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6633	Remote Similarity	NPD4754	Approved
0.6633	Remote Similarity	NPD5175	Approved
0.6633	Remote Similarity	NPD5174	Approved
0.6629	Remote Similarity	NPD7521	Approved
0.6629	Remote Similarity	NPD7146	Approved
0.6629	Remote Similarity	NPD7334	Approved
0.6629	Remote Similarity	NPD6684	Approved
0.6629	Remote Similarity	NPD5330	Approved
0.6629	Remote Similarity	NPD6409	Approved
0.6596	Remote Similarity	NPD5695	Phase 3
0.6591	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6683	Phase 2
0.6566	Remote Similarity	NPD5141	Approved
0.6562	Remote Similarity	NPD5290	Discontinued
0.6556	Remote Similarity	NPD3573	Approved
0.6552	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5776	Phase 2
0.6548	Remote Similarity	NPD6925	Approved
0.6535	Remote Similarity	NPD6899	Approved
0.6535	Remote Similarity	NPD7320	Approved
0.6535	Remote Similarity	NPD6881	Approved
0.6522	Remote Similarity	NPD4096	Approved
0.6517	Remote Similarity	NPD6893	Approved
0.6512	Remote Similarity	NPD4748	Discontinued
0.6512	Remote Similarity	NPD7332	Phase 2
0.6512	Remote Similarity	NPD7514	Phase 3
0.6506	Remote Similarity	NPD4190	Phase 3
0.6506	Remote Similarity	NPD5275	Approved
0.65	Remote Similarity	NPD4767	Approved
0.65	Remote Similarity	NPD4768	Approved
0.6489	Remote Similarity	NPD7900	Approved
0.6489	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5737	Approved
0.6484	Remote Similarity	NPD6672	Approved
0.6484	Remote Similarity	NPD6903	Approved
0.6484	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7145	Approved
0.6471	Remote Similarity	NPD6372	Approved
0.6471	Remote Similarity	NPD6373	Approved
0.6452	Remote Similarity	NPD5281	Approved
0.6452	Remote Similarity	NPD6411	Approved
0.6452	Remote Similarity	NPD5284	Approved
0.6437	Remote Similarity	NPD6898	Phase 1
0.6436	Remote Similarity	NPD5701	Approved
0.6436	Remote Similarity	NPD5697	Approved
0.6421	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7102	Approved
0.6408	Remote Similarity	NPD6883	Approved
0.6408	Remote Similarity	NPD7290	Approved
0.6404	Remote Similarity	NPD3668	Phase 3
0.6392	Remote Similarity	NPD5696	Approved
0.6383	Remote Similarity	NPD6399	Phase 3
0.6374	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7524	Approved
0.6374	Remote Similarity	NPD7750	Discontinued
0.6373	Remote Similarity	NPD4730	Approved
0.6373	Remote Similarity	NPD4729	Approved
0.6373	Remote Similarity	NPD5128	Approved
0.6373	Remote Similarity	NPD6011	Approved
0.6346	Remote Similarity	NPD6847	Approved
0.6346	Remote Similarity	NPD6649	Approved
0.6346	Remote Similarity	NPD8130	Phase 1
0.6346	Remote Similarity	NPD6617	Approved
0.6346	Remote Similarity	NPD6650	Approved
0.6346	Remote Similarity	NPD6869	Approved
0.6346	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6013	Approved
0.6311	Remote Similarity	NPD6014	Approved
0.6311	Remote Similarity	NPD6012	Approved
0.6304	Remote Similarity	NPD4518	Approved
0.6301	Remote Similarity	NPD342	Phase 1
0.6296	Remote Similarity	NPD4137	Phase 3
0.6286	Remote Similarity	NPD6882	Approved
0.6286	Remote Similarity	NPD8297	Approved
0.6279	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5344	Discontinued
0.625	Remote Similarity	NPD4139	Approved
0.625	Remote Similarity	NPD6902	Approved
0.625	Remote Similarity	NPD4634	Approved
0.625	Remote Similarity	NPD5251	Approved
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD5169	Approved
0.625	Remote Similarity	NPD5247	Approved
0.625	Remote Similarity	NPD4692	Approved
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD5249	Phase 3
0.625	Remote Similarity	NPD5135	Approved
0.625	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6904	Approved
0.6237	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6080	Approved
0.6237	Remote Similarity	NPD6673	Approved
0.6237	Remote Similarity	NPD6101	Approved
0.622	Remote Similarity	NPD4691	Approved
0.622	Remote Similarity	NPD4747	Approved
0.6214	Remote Similarity	NPD5168	Approved
0.6211	Remote Similarity	NPD5133	Approved
0.62	Remote Similarity	NPD7632	Discontinued
0.619	Remote Similarity	NPD5217	Approved
0.619	Remote Similarity	NPD5216	Approved
0.619	Remote Similarity	NPD5127	Approved
0.619	Remote Similarity	NPD5215	Approved
0.619	Remote Similarity	NPD5733	Approved
0.6154	Remote Similarity	NPD1694	Approved
0.6146	Remote Similarity	NPD5282	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data