NPASS Compound

Structure

NPC56962 OpenBabel07101719252D 36 40 0 0 1 0 0 0 0 0999 V2000 -4.8363 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8997 -5.2985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6428 -5.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -3.5032 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 -3.4980 -4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8289 -5.1974 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 -4.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 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 1 0 0 0 0 0 0 0 0 0 -3.1379 -6.1485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6340 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5417 -4.0385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 7 10 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 27 1 0 0 0 0 13 14 1 0 0 0 0 13 26 1 0 0 0 0 14 29 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 0 0 0 0 16 29 1 0 0 0 0 17 1 1 1 0 0 0 17 18 1 0 0 0 0 18 26 1 1 0 0 0 19 27 1 6 0 0 0 19 29 1 0 0 0 0 20 28 1 1 0 0 0 20 30 1 0 0 0 0 21 25 1 0 0 0 0 21 31 1 1 0 0 0 22 28 1 1 0 0 0 22 32 1 0 0 0 0 23 30 1 6 0 0 0 23 33 1 0 0 0 0 24 28 1 0 0 0 0 24 34 2 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 26 27 1 1 0 0 0 27 5 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.36
Volume:	534.759
LogP:	2.624
LogD:	3.165
LogS:	-3.643
# Rotatable Bonds:	6
TPSA:	118.22
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.365
Synthetic Accessibility Score:	5.981
Fsp3:	0.967
Lipinski Rule-of-5:	Accepted
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:	-5.772
MDCK Permeability:	1.3737523659074213e-05
Pgp-inhibitor:	0.088
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.14
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.592
Plasma Protein Binding (PPB):	90.47447967529297%
Volume Distribution (VD):	0.571
Pgp-substrate:	6.277892589569092%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.322
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.693
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.103
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.502
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	2.933
Half-life (T1/2):	0.447

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.636
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.675
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.832
Carcinogencity:	0.811
Eye Corrosion:	0.029
Eye Irritation:	0.019
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC56962

Natural Product ID:	NPC56962
*Common Name:**	WWIHQMXKPHUIKR-UVFBOVLQSA-N
IUPAC Name:	n.a.
Synonyms:	24-Epiquadrangularic Acid L
Standard InCHIKey:	WWIHQMXKPHUIKR-UVFBOVLQSA-N
Standard InCHI:	InChI=1S/C30H50O6/c1-17(7-10-21(31)25(2,3)36)18-11-12-27(5)19-8-9-20-28(6,24(34)35)22(32)15-23(33)30(20)16-29(19,30)14-13-26(18,27)4/h17-23,31-33,36H,7-16H2,1-6H3,(H,34,35)/t17-,18-,19+,20+,21+,22+,23+,26-,27+,28+,29+,30-/m1/s1
SMILES:	C[C@@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)[C@@H](O)C[C@@H]([C@@]2(C)C(=O)O)O)C)CC[C@@H](C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514459
PubChem CID:	10649269
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]

☑ 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
ED50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	100.0	ug ml-1	PMID[470779]

☑ 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 NPC56962 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	410
0.1-0.2	3370
0.2-0.3	9018
0.3-0.4	13882
0.4-0.5	5923
0.5-0.6	5398
0.6-0.7	3648
0.7-0.8	914
0.8-0.85	105
0.85-0.9	23
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC24705
0.9639	High Similarity	NPC302111
0.907	High Similarity	NPC263802
0.9036	High Similarity	NPC12933
0.8953	High Similarity	NPC472272
0.8941	High Similarity	NPC50438
0.8916	High Similarity	NPC477851
0.8791	High Similarity	NPC263135
0.8791	High Similarity	NPC288906
0.8706	High Similarity	NPC121121
0.8675	High Similarity	NPC224802
0.8675	High Similarity	NPC80089
0.8675	High Similarity	NPC324700
0.8675	High Similarity	NPC34046
0.8675	High Similarity	NPC171426
0.8571	High Similarity	NPC201276
0.8571	High Similarity	NPC80891
0.8571	High Similarity	NPC320144
0.8506	High Similarity	NPC319909
0.8506	High Similarity	NPC471044
0.8506	High Similarity	NPC473336
0.8495	Intermediate Similarity	NPC116683
0.8495	Intermediate Similarity	NPC234564
0.8452	Intermediate Similarity	NPC185465
0.8444	Intermediate Similarity	NPC61688
0.8434	Intermediate Similarity	NPC4209
0.8427	Intermediate Similarity	NPC202937
0.8421	Intermediate Similarity	NPC37047
0.8421	Intermediate Similarity	NPC180733
0.8421	Intermediate Similarity	NPC94906
0.8421	Intermediate Similarity	NPC41971
0.8409	Intermediate Similarity	NPC131350
0.8409	Intermediate Similarity	NPC473350
0.8387	Intermediate Similarity	NPC62407
0.8387	Intermediate Similarity	NPC287354
0.8387	Intermediate Similarity	NPC17336
0.837	Intermediate Similarity	NPC476189
0.8352	Intermediate Similarity	NPC77756
0.8333	Intermediate Similarity	NPC207010
0.8333	Intermediate Similarity	NPC226491
0.8333	Intermediate Similarity	NPC317913
0.8333	Intermediate Similarity	NPC477614
0.8333	Intermediate Similarity	NPC71706
0.8333	Intermediate Similarity	NPC264602
0.8316	Intermediate Similarity	NPC472028
0.8315	Intermediate Similarity	NPC476727
0.8315	Intermediate Similarity	NPC476726
0.8315	Intermediate Similarity	NPC83242
0.8315	Intermediate Similarity	NPC80700
0.8313	Intermediate Similarity	NPC212733
0.8295	Intermediate Similarity	NPC477434
0.8276	Intermediate Similarity	NPC154043
0.8276	Intermediate Similarity	NPC202688
0.8276	Intermediate Similarity	NPC268040
0.8276	Intermediate Similarity	NPC60018
0.8276	Intermediate Similarity	NPC477935
0.8276	Intermediate Similarity	NPC317066
0.8265	Intermediate Similarity	NPC201763
0.8261	Intermediate Similarity	NPC52756
0.8247	Intermediate Similarity	NPC193934
0.8247	Intermediate Similarity	NPC271980
0.8247	Intermediate Similarity	NPC124544
0.8211	Intermediate Similarity	NPC170978
0.8193	Intermediate Similarity	NPC280026
0.8193	Intermediate Similarity	NPC167702
0.8193	Intermediate Similarity	NPC477930
0.8191	Intermediate Similarity	NPC266431
0.8191	Intermediate Similarity	NPC470031
0.8163	Intermediate Similarity	NPC312900
0.8161	Intermediate Similarity	NPC476071
0.8161	Intermediate Similarity	NPC469745
0.8152	Intermediate Similarity	NPC476296
0.8144	Intermediate Similarity	NPC75941
0.8132	Intermediate Similarity	NPC146937
0.8132	Intermediate Similarity	NPC476379
0.8132	Intermediate Similarity	NPC476435
0.8118	Intermediate Similarity	NPC143133
0.8118	Intermediate Similarity	NPC477919
0.8118	Intermediate Similarity	NPC298168
0.8118	Intermediate Similarity	NPC475031
0.8118	Intermediate Similarity	NPC180199
0.8111	Intermediate Similarity	NPC114378
0.8111	Intermediate Similarity	NPC103782
0.81	Intermediate Similarity	NPC263729
0.8095	Intermediate Similarity	NPC273366
0.8095	Intermediate Similarity	NPC159789
0.809	Intermediate Similarity	NPC237938
0.809	Intermediate Similarity	NPC219535
0.8085	Intermediate Similarity	NPC470423
0.8068	Intermediate Similarity	NPC30583
0.8068	Intermediate Similarity	NPC289486
0.8068	Intermediate Similarity	NPC477936
0.8068	Intermediate Similarity	NPC61107
0.8061	Intermediate Similarity	NPC471254
0.8046	Intermediate Similarity	NPC470609
0.8023	Intermediate Similarity	NPC199965
0.8023	Intermediate Similarity	NPC147993
0.8023	Intermediate Similarity	NPC476732
0.8022	Intermediate Similarity	NPC239938
0.8022	Intermediate Similarity	NPC252714
0.8021	Intermediate Similarity	NPC472273
0.802	Intermediate Similarity	NPC163216
0.8	Intermediate Similarity	NPC477932
0.8	Intermediate Similarity	NPC266651
0.8	Intermediate Similarity	NPC82633
0.8	Intermediate Similarity	NPC474020
0.8	Intermediate Similarity	NPC477933
0.8	Intermediate Similarity	NPC472487
0.8	Intermediate Similarity	NPC477205
0.8	Intermediate Similarity	NPC472486
0.7978	Intermediate Similarity	NPC268578
0.7978	Intermediate Similarity	NPC327451
0.7978	Intermediate Similarity	NPC217559
0.7978	Intermediate Similarity	NPC292458
0.7978	Intermediate Similarity	NPC259173
0.7957	Intermediate Similarity	NPC475056
0.7957	Intermediate Similarity	NPC472146
0.7957	Intermediate Similarity	NPC185529
0.7955	Intermediate Similarity	NPC58631
0.7941	Intermediate Similarity	NPC285298
0.7941	Intermediate Similarity	NPC257082
0.7935	Intermediate Similarity	NPC56777
0.7935	Intermediate Similarity	NPC201607
0.7931	Intermediate Similarity	NPC287452
0.7917	Intermediate Similarity	NPC163685
0.7917	Intermediate Similarity	NPC235109
0.7912	Intermediate Similarity	NPC155531
0.7912	Intermediate Similarity	NPC215968
0.7912	Intermediate Similarity	NPC474448
0.7912	Intermediate Similarity	NPC472745
0.7907	Intermediate Similarity	NPC477918
0.7907	Intermediate Similarity	NPC221420
0.7895	Intermediate Similarity	NPC277399
0.7895	Intermediate Similarity	NPC477495
0.7895	Intermediate Similarity	NPC470424
0.7882	Intermediate Similarity	NPC158208
0.7882	Intermediate Similarity	NPC243027
0.7882	Intermediate Similarity	NPC477934
0.7882	Intermediate Similarity	NPC196136
0.7882	Intermediate Similarity	NPC125767
0.7882	Intermediate Similarity	NPC21220
0.7879	Intermediate Similarity	NPC470172
0.7872	Intermediate Similarity	NPC198242
0.7872	Intermediate Similarity	NPC211403
0.7865	Intermediate Similarity	NPC100366
0.7865	Intermediate Similarity	NPC242771
0.7865	Intermediate Similarity	NPC164289
0.7865	Intermediate Similarity	NPC13494
0.7865	Intermediate Similarity	NPC311642
0.7857	Intermediate Similarity	NPC232112
0.7849	Intermediate Similarity	NPC200580
0.7849	Intermediate Similarity	NPC477443
0.7849	Intermediate Similarity	NPC57954
0.7849	Intermediate Similarity	NPC67653
0.7849	Intermediate Similarity	NPC213832
0.7849	Intermediate Similarity	NPC477440
0.7849	Intermediate Similarity	NPC471459
0.7843	Intermediate Similarity	NPC469826
0.7841	Intermediate Similarity	NPC261616
0.7835	Intermediate Similarity	NPC469810
0.7835	Intermediate Similarity	NPC471241
0.7835	Intermediate Similarity	NPC253586
0.7831	Intermediate Similarity	NPC477850
0.7826	Intermediate Similarity	NPC5943
0.7822	Intermediate Similarity	NPC470587
0.7816	Intermediate Similarity	NPC329117
0.78	Intermediate Similarity	NPC473406
0.78	Intermediate Similarity	NPC471253
0.78	Intermediate Similarity	NPC34562
0.7791	Intermediate Similarity	NPC475742
0.7791	Intermediate Similarity	NPC5767
0.7789	Intermediate Similarity	NPC244356
0.7789	Intermediate Similarity	NPC224060
0.7789	Intermediate Similarity	NPC291373
0.7778	Intermediate Similarity	NPC46848
0.7778	Intermediate Similarity	NPC477285
0.7778	Intermediate Similarity	NPC472744
0.7778	Intermediate Similarity	NPC111582
0.7766	Intermediate Similarity	NPC477444
0.7766	Intermediate Similarity	NPC475211
0.7766	Intermediate Similarity	NPC477442
0.7766	Intermediate Similarity	NPC477433
0.7766	Intermediate Similarity	NPC88337
0.7765	Intermediate Similarity	NPC228994
0.7765	Intermediate Similarity	NPC192501
0.7765	Intermediate Similarity	NPC10476
0.7755	Intermediate Similarity	NPC472144
0.7755	Intermediate Similarity	NPC253995
0.7755	Intermediate Similarity	NPC476294
0.7753	Intermediate Similarity	NPC190940
0.7753	Intermediate Similarity	NPC254123
0.7745	Intermediate Similarity	NPC166993
0.7742	Intermediate Similarity	NPC473319
0.7742	Intermediate Similarity	NPC3032
0.7742	Intermediate Similarity	NPC131104
0.7742	Intermediate Similarity	NPC471221
0.7742	Intermediate Similarity	NPC471900
0.7738	Intermediate Similarity	NPC156277
0.7738	Intermediate Similarity	NPC473267
0.7738	Intermediate Similarity	NPC58057

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 NPC56962 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	441
0.1-0.2	3592
0.2-0.3	3389
0.3-0.4	1038
0.4-0.5	317
0.5-0.6	229
0.6-0.7	118
0.7-0.8	18
0.8-0.85	4
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8675	High Similarity	NPD6114	Approved
0.8675	High Similarity	NPD6697	Approved
0.8675	High Similarity	NPD6115	Approved
0.8675	High Similarity	NPD6118	Approved
0.8434	Intermediate Similarity	NPD6117	Approved
0.8333	Intermediate Similarity	NPD6116	Phase 1
0.8193	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD3703	Phase 2
0.7738	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5360	Phase 3
0.7381	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6081	Approved
0.7273	Intermediate Similarity	NPD3702	Approved
0.7255	Intermediate Similarity	NPD1700	Approved
0.7209	Intermediate Similarity	NPD4789	Approved
0.7209	Intermediate Similarity	NPD4245	Approved
0.7209	Intermediate Similarity	NPD4244	Approved
0.717	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4224	Phase 2
0.7093	Intermediate Similarity	NPD3698	Phase 2
0.7048	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8418	Phase 2
0.697	Remote Similarity	NPD8034	Phase 2
0.697	Remote Similarity	NPD8035	Phase 2
0.6932	Remote Similarity	NPD5777	Approved
0.6932	Remote Similarity	NPD4758	Discontinued
0.6881	Remote Similarity	NPD4634	Approved
0.6848	Remote Similarity	NPD5364	Discontinued
0.6848	Remote Similarity	NPD3671	Phase 1
0.6822	Remote Similarity	NPD6675	Approved
0.6822	Remote Similarity	NPD7128	Approved
0.6822	Remote Similarity	NPD5739	Approved
0.6822	Remote Similarity	NPD6402	Approved
0.6783	Remote Similarity	NPD6319	Approved
0.6768	Remote Similarity	NPD5328	Approved
0.675	Remote Similarity	NPD7319	Approved
0.6697	Remote Similarity	NPD7320	Approved
0.6697	Remote Similarity	NPD6899	Approved
0.6697	Remote Similarity	NPD6881	Approved
0.6696	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6636	Remote Similarity	NPD6372	Approved
0.6636	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6373	Approved
0.6635	Remote Similarity	NPD4755	Approved
0.6634	Remote Similarity	NPD6079	Approved
0.6629	Remote Similarity	NPD4787	Phase 1
0.6607	Remote Similarity	NPD8297	Approved
0.6606	Remote Similarity	NPD5701	Approved
0.6606	Remote Similarity	NPD5697	Approved
0.6577	Remote Similarity	NPD7290	Approved
0.6577	Remote Similarity	NPD7102	Approved
0.6577	Remote Similarity	NPD6883	Approved
0.6571	Remote Similarity	NPD7638	Approved
0.6555	Remote Similarity	NPD7492	Approved
0.6549	Remote Similarity	NPD8133	Approved
0.6529	Remote Similarity	NPD7736	Approved
0.6522	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6649	Approved
0.6518	Remote Similarity	NPD6869	Approved
0.6518	Remote Similarity	NPD6847	Approved
0.6518	Remote Similarity	NPD6650	Approved
0.6518	Remote Similarity	NPD6617	Approved
0.6518	Remote Similarity	NPD8130	Phase 1
0.6509	Remote Similarity	NPD5285	Approved
0.6509	Remote Similarity	NPD5286	Approved
0.6509	Remote Similarity	NPD7639	Approved
0.6509	Remote Similarity	NPD7640	Approved
0.6509	Remote Similarity	NPD4696	Approved
0.6509	Remote Similarity	NPD4700	Approved
0.65	Remote Similarity	NPD6616	Approved
0.65	Remote Similarity	NPD7507	Approved
0.6496	Remote Similarity	NPD6059	Approved
0.6496	Remote Similarity	NPD6054	Approved
0.6495	Remote Similarity	NPD4788	Approved
0.6486	Remote Similarity	NPD6012	Approved
0.6486	Remote Similarity	NPD6014	Approved
0.6486	Remote Similarity	NPD6013	Approved
0.6471	Remote Similarity	NPD7604	Phase 2
0.6471	Remote Similarity	NPD7515	Phase 2
0.646	Remote Similarity	NPD6882	Approved
0.6446	Remote Similarity	NPD7078	Approved
0.6446	Remote Similarity	NPD8293	Discontinued
0.6441	Remote Similarity	NPD6921	Approved
0.6435	Remote Similarity	NPD6940	Discontinued
0.6429	Remote Similarity	NPD4786	Approved
0.6408	Remote Similarity	NPD6399	Phase 3
0.6396	Remote Similarity	NPD6011	Approved
0.6389	Remote Similarity	NPD5225	Approved
0.6389	Remote Similarity	NPD7632	Discontinued
0.6389	Remote Similarity	NPD5226	Approved
0.6389	Remote Similarity	NPD5224	Approved
0.6389	Remote Similarity	NPD4633	Approved
0.6389	Remote Similarity	NPD5211	Phase 2
0.6387	Remote Similarity	NPD6370	Approved
0.6381	Remote Similarity	NPD5222	Approved
0.6381	Remote Similarity	NPD5221	Approved
0.6381	Remote Similarity	NPD4697	Phase 3
0.6381	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6009	Approved
0.6372	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6008	Approved
0.6354	Remote Similarity	NPD6928	Phase 2
0.6354	Remote Similarity	NPD7525	Registered
0.633	Remote Similarity	NPD5174	Approved
0.633	Remote Similarity	NPD5175	Approved
0.6322	Remote Similarity	NPD7909	Approved
0.6321	Remote Similarity	NPD5173	Approved
0.6321	Remote Similarity	NPD6084	Phase 2
0.6321	Remote Similarity	NPD6083	Phase 2
0.6303	Remote Similarity	NPD6016	Approved
0.6303	Remote Similarity	NPD6015	Approved
0.63	Remote Similarity	NPD3618	Phase 1
0.6296	Remote Similarity	NPD5223	Approved
0.6283	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5141	Approved
0.6261	Remote Similarity	NPD8298	Phase 2
0.625	Remote Similarity	NPD5988	Approved
0.625	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD8171	Discontinued
0.6235	Remote Similarity	NPD3198	Approved
0.6224	Remote Similarity	NPD3667	Approved
0.6216	Remote Similarity	NPD4767	Approved
0.6216	Remote Similarity	NPD4768	Approved
0.6198	Remote Similarity	NPD8328	Phase 3
0.6195	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7748	Approved
0.6182	Remote Similarity	NPD4754	Approved
0.6167	Remote Similarity	NPD5983	Phase 2
0.6154	Remote Similarity	NPD6274	Approved
0.6154	Remote Similarity	NPD6411	Approved
0.6154	Remote Similarity	NPD7637	Suspended
0.6146	Remote Similarity	NPD4802	Phase 2
0.6146	Remote Similarity	NPD4238	Approved
0.6139	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7100	Approved
0.6134	Remote Similarity	NPD7101	Approved
0.6132	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4753	Phase 2
0.6106	Remote Similarity	NPD4729	Approved
0.6106	Remote Similarity	NPD4730	Approved
0.6106	Remote Similarity	NPD5128	Approved
0.6098	Remote Similarity	NPD6336	Discontinued
0.605	Remote Similarity	NPD6335	Approved
0.605	Remote Similarity	NPD7328	Approved
0.605	Remote Similarity	NPD7327	Approved
0.6033	Remote Similarity	NPD6909	Approved
0.6033	Remote Similarity	NPD6908	Approved
0.6024	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7902	Approved
0.6018	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6412	Phase 2
0.6017	Remote Similarity	NPD6868	Approved
0.6	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD5250	Approved
0.6	Remote Similarity	NPD5249	Phase 3
0.6	Remote Similarity	NPD6033	Approved
0.6	Remote Similarity	NPD5248	Approved
0.6	Remote Similarity	NPD5247	Approved
0.6	Remote Similarity	NPD5251	Approved
0.5982	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5695	Phase 3
0.5966	Remote Similarity	NPD6317	Approved
0.5963	Remote Similarity	NPD5696	Approved
0.5963	Remote Similarity	NPD4225	Approved
0.5962	Remote Similarity	NPD6101	Approved
0.5962	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.596	Remote Similarity	NPD1779	Approved
0.596	Remote Similarity	NPD1780	Approved
0.5955	Remote Similarity	NPD371	Approved
0.5948	Remote Similarity	NPD5217	Approved
0.5948	Remote Similarity	NPD5215	Approved
0.5948	Remote Similarity	NPD5216	Approved
0.5943	Remote Similarity	NPD5778	Approved
0.5943	Remote Similarity	NPD5779	Approved
0.5941	Remote Similarity	NPD3133	Approved
0.5941	Remote Similarity	NPD3665	Phase 1
0.5941	Remote Similarity	NPD3666	Approved
0.5929	Remote Similarity	NPD6920	Discontinued
0.5917	Remote Similarity	NPD6314	Approved
0.5917	Remote Similarity	NPD6313	Approved
0.5905	Remote Similarity	NPD6700	Approved
0.5905	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD8380	Approved
0.5902	Remote Similarity	NPD8379	Approved
0.5902	Remote Similarity	NPD8378	Approved
0.5902	Remote Similarity	NPD8296	Approved
0.5902	Remote Similarity	NPD8335	Approved
0.5865	Remote Similarity	NPD6672	Approved
0.5865	Remote Similarity	NPD5737	Approved
0.5865	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5135	Approved
0.5862	Remote Similarity	NPD5134	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