NPASS Compound

Structure

NPC116683 OpenBabel07101718222D 29 33 0 0 1 0 0 0 0 0999 V2000 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 1.3090 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5209 0.3971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6397 -0.9598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1502 -0.3800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 2.5873 0.0388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1488 -0.3277 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5782 1.0387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6056 -1.2187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 7 1 0 0 0 0 3 14 1 0 0 0 0 4 8 1 0 0 0 0 4 15 1 0 0 0 0 5 9 1 0 0 0 0 5 16 1 0 0 0 0 6 10 1 0 0 0 0 6 17 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 21 1 0 0 0 0 13 29 1 0 0 0 0 14 24 1 1 0 0 0 15 16 1 0 0 0 0 15 19 1 1 0 0 0 16 23 1 6 0 0 0 17 20 1 1 0 0 0 17 21 1 0 0 0 0 18 25 2 0 0 0 0 18 29 1 0 0 0 0 19 22 1 1 0 0 0 20 23 1 1 0 0 0 21 26 1 6 0 0 0 22 27 1 1 0 0 0 23 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.25
Volume:	413.687
LogP:	1.581
LogD:	1.037
LogS:	-3.374
# Rotatable Bonds:	1
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.494
Synthetic Accessibility Score:	4.971
Fsp3:	0.957
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.425
MDCK Permeability:	2.498691901564598e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.428
Plasma Protein Binding (PPB):	24.00790023803711%
Volume Distribution (VD):	0.443
Pgp-substrate:	37.8305778503418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.853
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.584
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.848
CYP3A4-substrate:	0.357

ADMET: Excretion

Clearance (CL):	3.998
Half-life (T1/2):	0.28

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.509
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.292
Carcinogencity:	0.838
Eye Corrosion:	0.025
Eye Irritation:	0.033
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC116683

Natural Product ID:	NPC116683
*Common Name:**	Antiarotoxinin A
IUPAC Name:	(4S)-4-hydroxy-4-[(3S,5S,8R,9S,10R,13R,14S,17S)-3,5,14-trihydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]oxolan-2-one
Synonyms:	Antiarotoxinin A
Standard InCHIKey:	ZLVFJNWHRCVCMX-PZLUUTJLSA-N
Standard InCHI:	InChI=1S/C23H36O6/c1-19-7-3-14(24)11-22(19,27)9-5-16-15(19)4-8-20(2)17(6-10-23(16,20)28)21(26)12-18(25)29-13-21/h14-17,24,26-28H,3-13H2,1-2H3/t14-,15-,16+,17-,19+,20+,21+,22-,23-/m0/s1
SMILES:	C[C@@]12CC[C@@H](C[C@]2(CC[C@@H]2[C@@H]1CC[C@]1(C)[C@H](CC[C@]21O)[C@]1(CC(=O)OC1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1173656
PubChem CID:	46872818
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides 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
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20553004]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	latex	Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Yunnan Province, China	2011-Mar	PMID[24033101]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	trunk bark	Yunnan, China	n.a.	PMID[24582402]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8369	Antiaris toxicaria	Species	Moraceae	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
ED50	2
Others	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	15.0	ug ml-1	PMID[469181]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	4.3	ug ml-1	PMID[469181]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.1	uM	PMID[469180]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	367.0	%	PMID[469180]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	1000.0	n.a.	PMID[469180]

☑ 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 NPC116683 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	427
0.1-0.2	3271
0.2-0.3	7974
0.3-0.4	14193
0.4-0.5	5917
0.5-0.6	5233
0.6-0.7	4088
0.7-0.8	1400
0.8-0.85	149
0.85-0.9	42
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8817	High Similarity	NPC476189
0.8791	High Similarity	NPC471221
0.8778	High Similarity	NPC215968
0.8778	High Similarity	NPC155531
0.875	High Similarity	NPC253995
0.8723	High Similarity	NPC470424
0.8723	High Similarity	NPC206878
0.8696	High Similarity	NPC61688
0.8687	High Similarity	NPC100078
0.8673	High Similarity	NPC244969
0.8673	High Similarity	NPC213528
0.8667	High Similarity	NPC266651
0.866	High Similarity	NPC108371
0.8602	High Similarity	NPC470114
0.86	High Similarity	NPC166079
0.8587	High Similarity	NPC201607
0.8587	High Similarity	NPC56777
0.8571	High Similarity	NPC103782
0.8571	High Similarity	NPC114378
0.8571	High Similarity	NPC178853
0.8571	High Similarity	NPC477283
0.8571	High Similarity	NPC472272
0.8556	High Similarity	NPC471044
0.8556	High Similarity	NPC473336
0.8539	High Similarity	NPC477935
0.8539	High Similarity	NPC477936
0.8511	High Similarity	NPC473066
0.8495	Intermediate Similarity	NPC24705
0.8495	Intermediate Similarity	NPC56962
0.8485	Intermediate Similarity	NPC470172
0.8454	Intermediate Similarity	NPC253586
0.8454	Intermediate Similarity	NPC471241
0.8444	Intermediate Similarity	NPC268578
0.8444	Intermediate Similarity	NPC111582
0.8444	Intermediate Similarity	NPC217559
0.8444	Intermediate Similarity	NPC292458
0.8444	Intermediate Similarity	NPC477285
0.8438	Intermediate Similarity	NPC62407
0.8438	Intermediate Similarity	NPC287354
0.8427	Intermediate Similarity	NPC58631
0.8421	Intermediate Similarity	NPC122083
0.8421	Intermediate Similarity	NPC211845
0.8421	Intermediate Similarity	NPC256104
0.8421	Intermediate Similarity	NPC182740
0.8416	Intermediate Similarity	NPC306776
0.84	Intermediate Similarity	NPC471253
0.84	Intermediate Similarity	NPC473406
0.8387	Intermediate Similarity	NPC476379
0.8387	Intermediate Similarity	NPC476435
0.837	Intermediate Similarity	NPC474448
0.837	Intermediate Similarity	NPC80700
0.837	Intermediate Similarity	NPC92139
0.8352	Intermediate Similarity	NPC65133
0.8352	Intermediate Similarity	NPC473299
0.8351	Intermediate Similarity	NPC476728
0.8333	Intermediate Similarity	NPC286719
0.8333	Intermediate Similarity	NPC311642
0.8333	Intermediate Similarity	NPC164289
0.8333	Intermediate Similarity	NPC202688
0.8333	Intermediate Similarity	NPC13494
0.8333	Intermediate Similarity	NPC154043
0.8333	Intermediate Similarity	NPC477495
0.8333	Intermediate Similarity	NPC60018
0.8333	Intermediate Similarity	NPC100366
0.8333	Intermediate Similarity	NPC121121
0.8333	Intermediate Similarity	NPC470423
0.8333	Intermediate Similarity	NPC242771
0.8333	Intermediate Similarity	NPC477286
0.8317	Intermediate Similarity	NPC88469
0.8302	Intermediate Similarity	NPC79193
0.8302	Intermediate Similarity	NPC470115
0.8302	Intermediate Similarity	NPC470116
0.83	Intermediate Similarity	NPC471254
0.8298	Intermediate Similarity	NPC200580
0.828	Intermediate Similarity	NPC263802
0.828	Intermediate Similarity	NPC5943
0.8261	Intermediate Similarity	NPC473350
0.8247	Intermediate Similarity	NPC17336
0.8247	Intermediate Similarity	NPC215570
0.8242	Intermediate Similarity	NPC259173
0.8235	Intermediate Similarity	NPC472655
0.8229	Intermediate Similarity	NPC472232
0.8229	Intermediate Similarity	NPC472231
0.8224	Intermediate Similarity	NPC475490
0.8222	Intermediate Similarity	NPC190940
0.8211	Intermediate Similarity	NPC77756
0.8208	Intermediate Similarity	NPC102619
0.8208	Intermediate Similarity	NPC97002
0.8202	Intermediate Similarity	NPC201276
0.8202	Intermediate Similarity	NPC477282
0.8202	Intermediate Similarity	NPC476176
0.8202	Intermediate Similarity	NPC81074
0.8202	Intermediate Similarity	NPC80891
0.82	Intermediate Similarity	NPC259654
0.82	Intermediate Similarity	NPC298266
0.8191	Intermediate Similarity	NPC226491
0.8191	Intermediate Similarity	NPC477614
0.819	Intermediate Similarity	NPC469824
0.819	Intermediate Similarity	NPC473062
0.8182	Intermediate Similarity	NPC472144
0.8172	Intermediate Similarity	NPC302111
0.8172	Intermediate Similarity	NPC131365
0.8163	Intermediate Similarity	NPC193785
0.8163	Intermediate Similarity	NPC235109
0.8163	Intermediate Similarity	NPC475785
0.8163	Intermediate Similarity	NPC156377
0.8152	Intermediate Similarity	NPC477434
0.8152	Intermediate Similarity	NPC291310
0.8152	Intermediate Similarity	NPC50438
0.8148	Intermediate Similarity	NPC179429
0.8137	Intermediate Similarity	NPC473701
0.8137	Intermediate Similarity	NPC327093
0.8137	Intermediate Similarity	NPC473526
0.8132	Intermediate Similarity	NPC475388
0.8132	Intermediate Similarity	NPC102156
0.8132	Intermediate Similarity	NPC477284
0.8132	Intermediate Similarity	NPC148740
0.8125	Intermediate Similarity	NPC52756
0.8111	Intermediate Similarity	NPC470609
0.8111	Intermediate Similarity	NPC474714
0.8111	Intermediate Similarity	NPC472853
0.8105	Intermediate Similarity	NPC67653
0.8105	Intermediate Similarity	NPC471459
0.81	Intermediate Similarity	NPC477655
0.81	Intermediate Similarity	NPC477656
0.809	Intermediate Similarity	NPC224802
0.809	Intermediate Similarity	NPC80089
0.809	Intermediate Similarity	NPC476732
0.809	Intermediate Similarity	NPC171426
0.809	Intermediate Similarity	NPC34046
0.809	Intermediate Similarity	NPC199965
0.809	Intermediate Similarity	NPC324700
0.809	Intermediate Similarity	NPC471045
0.8085	Intermediate Similarity	NPC202937
0.8085	Intermediate Similarity	NPC210658
0.8085	Intermediate Similarity	NPC239938
0.8085	Intermediate Similarity	NPC161928
0.8081	Intermediate Similarity	NPC472273
0.8081	Intermediate Similarity	NPC472145
0.8065	Intermediate Similarity	NPC477445
0.8061	Intermediate Similarity	NPC21897
0.8061	Intermediate Similarity	NPC82633
0.8043	Intermediate Similarity	NPC69953
0.8041	Intermediate Similarity	NPC161035
0.8039	Intermediate Similarity	NPC107385
0.8022	Intermediate Similarity	NPC475743
0.8022	Intermediate Similarity	NPC12933
0.8021	Intermediate Similarity	NPC50443
0.8021	Intermediate Similarity	NPC185529
0.8021	Intermediate Similarity	NPC472146
0.8021	Intermediate Similarity	NPC18536
0.802	Intermediate Similarity	NPC475574
0.802	Intermediate Similarity	NPC477172
0.8019	Intermediate Similarity	NPC272242
0.8	Intermediate Similarity	NPC128475
0.8	Intermediate Similarity	NPC477287
0.8	Intermediate Similarity	NPC31302
0.8	Intermediate Similarity	NPC221993
0.8	Intermediate Similarity	NPC245029
0.7981	Intermediate Similarity	NPC166993
0.798	Intermediate Similarity	NPC163685
0.798	Intermediate Similarity	NPC475765
0.7979	Intermediate Similarity	NPC476726
0.7979	Intermediate Similarity	NPC83242
0.7979	Intermediate Similarity	NPC472745
0.7979	Intermediate Similarity	NPC476727
0.7978	Intermediate Similarity	NPC133596
0.7978	Intermediate Similarity	NPC171658
0.7978	Intermediate Similarity	NPC474574
0.7978	Intermediate Similarity	NPC317913
0.7978	Intermediate Similarity	NPC477919
0.7978	Intermediate Similarity	NPC11907
0.7978	Intermediate Similarity	NPC180199
0.7978	Intermediate Similarity	NPC64081
0.7978	Intermediate Similarity	NPC207010
0.7961	Intermediate Similarity	NPC470167
0.7961	Intermediate Similarity	NPC469827
0.7959	Intermediate Similarity	NPC247877
0.7959	Intermediate Similarity	NPC309127
0.7957	Intermediate Similarity	NPC319909
0.7944	Intermediate Similarity	NPC477489
0.7941	Intermediate Similarity	NPC124544
0.7938	Intermediate Similarity	NPC475878
0.7938	Intermediate Similarity	NPC474065
0.7935	Intermediate Similarity	NPC477446
0.7935	Intermediate Similarity	NPC470155
0.7935	Intermediate Similarity	NPC470611
0.7935	Intermediate Similarity	NPC477447
0.7935	Intermediate Similarity	NPC317066
0.7925	Intermediate Similarity	NPC106760
0.7921	Intermediate Similarity	NPC470030
0.7921	Intermediate Similarity	NPC41843
0.7921	Intermediate Similarity	NPC20028
0.7917	Intermediate Similarity	NPC477440
0.7917	Intermediate Similarity	NPC477443
0.7912	Intermediate Similarity	NPC472951
0.7912	Intermediate Similarity	NPC472943
0.7905	Intermediate Similarity	NPC469826
0.7905	Intermediate Similarity	NPC273155
0.7905	Intermediate Similarity	NPC112895

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 NPC116683 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	463
0.1-0.2	3448
0.2-0.3	3464
0.3-0.4	1012
0.4-0.5	362
0.5-0.6	239
0.6-0.7	126
0.7-0.8	32
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.809	Intermediate Similarity	NPD6115	Approved
0.809	Intermediate Similarity	NPD6114	Approved
0.809	Intermediate Similarity	NPD6118	Approved
0.809	Intermediate Similarity	NPD6697	Approved
0.802	Intermediate Similarity	NPD1700	Approved
0.7978	Intermediate Similarity	NPD6116	Phase 1
0.7865	Intermediate Similarity	NPD6117	Approved
0.7788	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3702	Approved
0.734	Intermediate Similarity	NPD6928	Phase 2
0.7327	Intermediate Similarity	NPD8171	Discontinued
0.725	Intermediate Similarity	NPD7319	Approved
0.7228	Intermediate Similarity	NPD8035	Phase 2
0.7228	Intermediate Similarity	NPD8034	Phase 2
0.7222	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5777	Approved
0.7203	Intermediate Similarity	NPD7492	Approved
0.7191	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3703	Phase 2
0.7167	Intermediate Similarity	NPD7736	Approved
0.7155	Intermediate Similarity	NPD6054	Approved
0.7155	Intermediate Similarity	NPD6059	Approved
0.7155	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD6616	Approved
0.7111	Intermediate Similarity	NPD4244	Approved
0.7111	Intermediate Similarity	NPD4245	Approved
0.7083	Intermediate Similarity	NPD7078	Approved
0.7083	Intermediate Similarity	NPD8293	Discontinued
0.708	Intermediate Similarity	NPD8133	Approved
0.7034	Intermediate Similarity	NPD6370	Approved
0.7	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD3698	Phase 2
0.7	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6016	Approved
0.6949	Remote Similarity	NPD6015	Approved
0.6937	Remote Similarity	NPD7320	Approved
0.693	Remote Similarity	NPD4632	Approved
0.6909	Remote Similarity	NPD6675	Approved
0.6909	Remote Similarity	NPD7128	Approved
0.6909	Remote Similarity	NPD6008	Approved
0.6909	Remote Similarity	NPD5739	Approved
0.6909	Remote Similarity	NPD6402	Approved
0.6891	Remote Similarity	NPD5988	Approved
0.6889	Remote Similarity	NPD5360	Phase 3
0.6889	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6372	Approved
0.6875	Remote Similarity	NPD6373	Approved
0.6875	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6081	Approved
0.6842	Remote Similarity	NPD8297	Approved
0.6838	Remote Similarity	NPD7327	Approved
0.6838	Remote Similarity	NPD7328	Approved
0.6822	Remote Similarity	NPD7638	Approved
0.6818	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6940	Discontinued
0.6786	Remote Similarity	NPD6899	Approved
0.6786	Remote Similarity	NPD6881	Approved
0.678	Remote Similarity	NPD7516	Approved
0.6759	Remote Similarity	NPD7640	Approved
0.6759	Remote Similarity	NPD7639	Approved
0.6754	Remote Similarity	NPD6649	Approved
0.6754	Remote Similarity	NPD6650	Approved
0.6752	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7115	Discovery
0.6739	Remote Similarity	NPD4789	Approved
0.6726	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6412	Phase 2
0.6696	Remote Similarity	NPD5697	Approved
0.6696	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4224	Phase 2
0.6667	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.6613	Remote Similarity	NPD6033	Approved
0.661	Remote Similarity	NPD6009	Approved
0.6609	Remote Similarity	NPD6847	Approved
0.6609	Remote Similarity	NPD6617	Approved
0.6609	Remote Similarity	NPD6869	Approved
0.6609	Remote Similarity	NPD8130	Phase 1
0.6606	Remote Similarity	NPD8418	Phase 2
0.6598	Remote Similarity	NPD4802	Phase 2
0.6598	Remote Similarity	NPD4238	Approved
0.6583	Remote Similarity	NPD8377	Approved
0.6583	Remote Similarity	NPD8294	Approved
0.6579	Remote Similarity	NPD6013	Approved
0.6579	Remote Similarity	NPD6012	Approved
0.6579	Remote Similarity	NPD6014	Approved
0.6574	Remote Similarity	NPD6083	Phase 2
0.6574	Remote Similarity	NPD6084	Phase 2
0.6559	Remote Similarity	NPD4787	Phase 1
0.6557	Remote Similarity	NPD7604	Phase 2
0.6556	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6882	Approved
0.6542	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD8033	Approved
0.6529	Remote Similarity	NPD5983	Phase 2
0.6491	Remote Similarity	NPD6011	Approved
0.6489	Remote Similarity	NPD4758	Discontinued
0.6466	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6336	Discontinued
0.6436	Remote Similarity	NPD3669	Approved
0.6436	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4788	Approved
0.6429	Remote Similarity	NPD5364	Discontinued
0.6429	Remote Similarity	NPD3671	Phase 1
0.6423	Remote Similarity	NPD8328	Phase 3
0.6422	Remote Similarity	NPD4755	Approved
0.6404	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1780	Approved
0.64	Remote Similarity	NPD1779	Approved
0.6389	Remote Similarity	NPD7991	Discontinued
0.6364	Remote Similarity	NPD5696	Approved
0.6364	Remote Similarity	NPD4225	Approved
0.6355	Remote Similarity	NPD4202	Approved
0.6344	Remote Similarity	NPD229	Approved
0.6306	Remote Similarity	NPD5286	Approved
0.6306	Remote Similarity	NPD5285	Approved
0.6306	Remote Similarity	NPD4700	Approved
0.6306	Remote Similarity	NPD4696	Approved
0.629	Remote Similarity	NPD6067	Discontinued
0.6273	Remote Similarity	NPD7902	Approved
0.6264	Remote Similarity	NPD371	Approved
0.626	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6274	Approved
0.6239	Remote Similarity	NPD5695	Phase 3
0.623	Remote Similarity	NPD7100	Approved
0.623	Remote Similarity	NPD7101	Approved
0.6211	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6686	Approved
0.6195	Remote Similarity	NPD5226	Approved
0.6195	Remote Similarity	NPD5225	Approved
0.6195	Remote Similarity	NPD5211	Phase 2
0.6195	Remote Similarity	NPD5224	Approved
0.6195	Remote Similarity	NPD4633	Approved
0.618	Remote Similarity	NPD3198	Approved
0.6148	Remote Similarity	NPD6335	Approved
0.6147	Remote Similarity	NPD6001	Approved
0.6147	Remote Similarity	NPD7748	Approved
0.614	Remote Similarity	NPD5175	Approved
0.614	Remote Similarity	NPD5174	Approved
0.6139	Remote Similarity	NPD7525	Registered
0.6134	Remote Similarity	NPD6053	Discontinued
0.6132	Remote Similarity	NPD6903	Approved
0.6132	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7503	Approved
0.6129	Remote Similarity	NPD6909	Approved
0.6129	Remote Similarity	NPD6908	Approved
0.6124	Remote Similarity	NPD5956	Approved
0.6121	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7515	Phase 2
0.6111	Remote Similarity	NPD7637	Suspended
0.6106	Remote Similarity	NPD5223	Approved
0.6102	Remote Similarity	NPD6371	Approved
0.6095	Remote Similarity	NPD7334	Approved
0.6095	Remote Similarity	NPD7146	Approved
0.6095	Remote Similarity	NPD7521	Approved
0.6095	Remote Similarity	NPD3618	Phase 1
0.6095	Remote Similarity	NPD6409	Approved
0.6095	Remote Similarity	NPD5330	Approved
0.6095	Remote Similarity	NPD6684	Approved
0.6095	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5141	Approved
0.6075	Remote Similarity	NPD4753	Phase 2
0.6075	Remote Similarity	NPD5328	Approved
0.6066	Remote Similarity	NPD6317	Approved
0.6058	Remote Similarity	NPD4786	Approved
0.6034	Remote Similarity	NPD4768	Approved
0.6034	Remote Similarity	NPD4767	Approved
0.6022	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6314	Approved
0.6016	Remote Similarity	NPD6313	Approved
0.6	Remote Similarity	NPD7900	Approved
0.6	Remote Similarity	NPD4754	Approved
0.6	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5281	Approved
0.5963	Remote Similarity	NPD6079	Approved
0.5963	Remote Similarity	NPD5284	Approved
0.5946	Remote Similarity	NPD5210	Approved
0.5946	Remote Similarity	NPD4629	Approved
0.5943	Remote Similarity	NPD6098	Approved
0.5932	Remote Similarity	NPD4729	Approved
0.5932	Remote Similarity	NPD4730	Approved
0.5932	Remote Similarity	NPD5128	Approved
0.5926	Remote Similarity	NPD6904	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data