NPASS Compound

Structure

NPC470070 OpenBabel07101718232D 33 38 0 0 1 0 0 0 0 0999 V2000 1.7304 -1.8198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0833 0.5026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5501 -0.3060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9853 -0.7728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3307 -1.1365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8703 0.8793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9588 1.5670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2269 1.3426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2052 0.4064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2052 -1.0183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7939 -0.7809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8516 1.3075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7939 0.6438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4765 0.3196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3824 -0.6093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0113 -0.3646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8077 -1.6772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0004 0.7593 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5483 -0.2589 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2052 -0.0685 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3826 -0.0685 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6164 -0.7809 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4852 0.3636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6164 -0.3060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7939 -0.3060 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3826 0.4064 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0113 0.7025 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6221 0.6962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4699 -0.8068 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2229 -2.4050 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4250 -1.2477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1527 -0.7437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 8 12 1 0 0 0 0 8 18 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 25 1 0 0 0 0 12 27 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 21 1 0 0 0 0 17 1 1 6 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 28 1 6 0 0 0 19 16 1 6 0 0 0 19 23 1 0 0 0 0 19 32 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 6 0 0 0 21 25 1 6 0 0 0 21 26 1 0 0 0 0 22 24 1 0 0 0 0 22 31 1 6 0 0 0 23 27 1 1 0 0 0 25 4 1 6 0 0 0 26 27 1 1 0 0 0 27 6 1 1 0 0 0 28 7 1 1 0 0 0 28 33 1 0 0 0 0 29 17 1 1 0 0 0 29 32 1 0 0 0 0 29 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.36
Volume:	493.962
LogP:	4.986
LogD:	4.841
LogS:	-4.502
# Rotatable Bonds:	1
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.528
Synthetic Accessibility Score:	5.981
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.988
MDCK Permeability:	5.790566501673311e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.152

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	93.45307922363281%
Volume Distribution (VD):	1.036
Pgp-substrate:	4.599406719207764%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.546
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.94
CYP2C9-inhibitor:	0.152
CYP2C9-substrate:	0.064
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.615
CYP3A4-inhibitor:	0.408
CYP3A4-substrate:	0.48

ADMET: Excretion

Clearance (CL):	7.461
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.396
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.456
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.793
Carcinogencity:	0.024
Eye Corrosion:	0.237
Eye Irritation:	0.109
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC470070

Natural Product ID:	NPC470070
*Common Name:**	APPPXTMUUWJGRZ-NNVISGGKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	APPPXTMUUWJGRZ-NNVISGGKSA-N
Standard InCHI:	InChI=1S/C29H48O4/c1-17(30)29-15-14-28(7,33-29)18-8-12-27(6)23(18)19(32-29)16-21-25(4)11-10-22(31)24(2,3)20(25)9-13-26(21,27)5/h17-23,30-31H,8-16H2,1-7H3/t17-,18-,19+,20-,21+,22-,23-,25-,26+,27+,28-,29-/m0/s1
SMILES:	C[C@@H]([C@@]12CC[C@@](O2)(C)[C@@H]2[C@H]3[C@H](O1)C[C@@H]1[C@@]4(C)CC[C@@H](C([C@@H]4CC[C@]1([C@]3(C)CC2)C)(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669122
PubChem CID:	53324794
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	48960.0	nM	PMID[509197]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	64140.0	nM	PMID[509197]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	70650.0	nM	PMID[509197]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	42390.0	nM	PMID[509197]

☑ 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 NPC470070 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	461
0.1-0.2	4419
0.2-0.3	14167
0.3-0.4	10455
0.4-0.5	5308
0.5-0.6	4947
0.6-0.7	2199
0.7-0.8	661
0.8-0.85	59
0.85-0.9	18
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9221	High Similarity	NPC64081
0.9221	High Similarity	NPC474574
0.9125	High Similarity	NPC470611
0.9036	High Similarity	NPC210658
0.9036	High Similarity	NPC161928
0.8987	High Similarity	NPC477282
0.8987	High Similarity	NPC81074
0.8974	High Similarity	NPC133596
0.8974	High Similarity	NPC11907
0.8961	High Similarity	NPC231680
0.8961	High Similarity	NPC91387
0.8961	High Similarity	NPC270306
0.8929	High Similarity	NPC128475
0.8824	High Similarity	NPC82955
0.8795	High Similarity	NPC273290
0.8795	High Similarity	NPC290612
0.8795	High Similarity	NPC232044
0.878	High Similarity	NPC477285
0.878	High Similarity	NPC111582
0.8675	High Similarity	NPC227260
0.8659	High Similarity	NPC286719
0.8659	High Similarity	NPC475388
0.8659	High Similarity	NPC296734
0.8659	High Similarity	NPC477286
0.8621	High Similarity	NPC210759
0.8621	High Similarity	NPC229801
0.8621	High Similarity	NPC307167
0.8605	High Similarity	NPC20822
0.8605	High Similarity	NPC228059
0.8588	High Similarity	NPC43912
0.8588	High Similarity	NPC140446
0.8537	High Similarity	NPC190940
0.8523	High Similarity	NPC256104
0.8523	High Similarity	NPC311246
0.8523	High Similarity	NPC167644
0.8523	High Similarity	NPC182740
0.8523	High Similarity	NPC211845
0.8523	High Similarity	NPC122083
0.8506	High Similarity	NPC473542
0.8471	Intermediate Similarity	NPC155531
0.8471	Intermediate Similarity	NPC215968
0.8427	Intermediate Similarity	NPC305418
0.8427	Intermediate Similarity	NPC45959
0.8427	Intermediate Similarity	NPC175
0.8427	Intermediate Similarity	NPC3538
0.8427	Intermediate Similarity	NPC113500
0.8427	Intermediate Similarity	NPC30687
0.8427	Intermediate Similarity	NPC477224
0.8427	Intermediate Similarity	NPC252253
0.8415	Intermediate Similarity	NPC257296
0.8415	Intermediate Similarity	NPC7479
0.8415	Intermediate Similarity	NPC248944
0.8409	Intermediate Similarity	NPC149966
0.8409	Intermediate Similarity	NPC5632
0.8409	Intermediate Similarity	NPC59006
0.8391	Intermediate Similarity	NPC131466
0.8333	Intermediate Similarity	NPC131506
0.8333	Intermediate Similarity	NPC473064
0.8333	Intermediate Similarity	NPC1340
0.8333	Intermediate Similarity	NPC252182
0.8333	Intermediate Similarity	NPC187471
0.8333	Intermediate Similarity	NPC157777
0.8333	Intermediate Similarity	NPC470071
0.8333	Intermediate Similarity	NPC473065
0.8333	Intermediate Similarity	NPC473067
0.8315	Intermediate Similarity	NPC88962
0.8315	Intermediate Similarity	NPC144790
0.8315	Intermediate Similarity	NPC149400
0.8312	Intermediate Similarity	NPC66407
0.8295	Intermediate Similarity	NPC279329
0.8276	Intermediate Similarity	NPC281004
0.8256	Intermediate Similarity	NPC477283
0.8256	Intermediate Similarity	NPC471240
0.825	Intermediate Similarity	NPC196136
0.825	Intermediate Similarity	NPC317242
0.825	Intermediate Similarity	NPC243027
0.825	Intermediate Similarity	NPC158208
0.8242	Intermediate Similarity	NPC203434
0.8242	Intermediate Similarity	NPC304011
0.8242	Intermediate Similarity	NPC237071
0.8242	Intermediate Similarity	NPC156377
0.8242	Intermediate Similarity	NPC476510
0.8242	Intermediate Similarity	NPC139271
0.8242	Intermediate Similarity	NPC142264
0.8242	Intermediate Similarity	NPC238796
0.8235	Intermediate Similarity	NPC320824
0.8228	Intermediate Similarity	NPC470610
0.8228	Intermediate Similarity	NPC153719
0.8222	Intermediate Similarity	NPC174024
0.8222	Intermediate Similarity	NPC473851
0.8222	Intermediate Similarity	NPC179859
0.8222	Intermediate Similarity	NPC291547
0.8222	Intermediate Similarity	NPC475436
0.8222	Intermediate Similarity	NPC473774
0.8222	Intermediate Similarity	NPC24960
0.8222	Intermediate Similarity	NPC131693
0.8222	Intermediate Similarity	NPC253268
0.8222	Intermediate Similarity	NPC312678
0.8214	Intermediate Similarity	NPC154043
0.8214	Intermediate Similarity	NPC60018
0.8214	Intermediate Similarity	NPC202688
0.8202	Intermediate Similarity	NPC36372
0.8202	Intermediate Similarity	NPC293609
0.8193	Intermediate Similarity	NPC16449
0.8182	Intermediate Similarity	NPC473472
0.8182	Intermediate Similarity	NPC102725
0.8171	Intermediate Similarity	NPC177343
0.8161	Intermediate Similarity	NPC472396
0.8152	Intermediate Similarity	NPC477222
0.8152	Intermediate Similarity	NPC470028
0.8152	Intermediate Similarity	NPC233649
0.8152	Intermediate Similarity	NPC477223
0.8148	Intermediate Similarity	NPC163597
0.8132	Intermediate Similarity	NPC21897
0.8132	Intermediate Similarity	NPC474399
0.8125	Intermediate Similarity	NPC10476
0.8125	Intermediate Similarity	NPC48795
0.8125	Intermediate Similarity	NPC192501
0.8125	Intermediate Similarity	NPC228994
0.8111	Intermediate Similarity	NPC325828
0.8111	Intermediate Similarity	NPC250393
0.8111	Intermediate Similarity	NPC177834
0.8111	Intermediate Similarity	NPC477451
0.8111	Intermediate Similarity	NPC477547
0.8111	Intermediate Similarity	NPC249204
0.8111	Intermediate Similarity	NPC141769
0.8111	Intermediate Similarity	NPC277774
0.8111	Intermediate Similarity	NPC234352
0.8111	Intermediate Similarity	NPC48339
0.8111	Intermediate Similarity	NPC297348
0.8101	Intermediate Similarity	NPC100586
0.8101	Intermediate Similarity	NPC157422
0.8101	Intermediate Similarity	NPC127094
0.8101	Intermediate Similarity	NPC109457
0.809	Intermediate Similarity	NPC65550
0.809	Intermediate Similarity	NPC223143
0.8077	Intermediate Similarity	NPC107919
0.8072	Intermediate Similarity	NPC477287
0.8068	Intermediate Similarity	NPC201607
0.8068	Intermediate Similarity	NPC56777
0.8065	Intermediate Similarity	NPC473638
0.8049	Intermediate Similarity	NPC128951
0.8049	Intermediate Similarity	NPC105208
0.8049	Intermediate Similarity	NPC185915
0.8049	Intermediate Similarity	NPC192046
0.8049	Intermediate Similarity	NPC477227
0.8049	Intermediate Similarity	NPC302578
0.8046	Intermediate Similarity	NPC103782
0.8046	Intermediate Similarity	NPC471410
0.8046	Intermediate Similarity	NPC80700
0.8046	Intermediate Similarity	NPC114378
0.8046	Intermediate Similarity	NPC471411
0.8043	Intermediate Similarity	NPC476728
0.8043	Intermediate Similarity	NPC121453
0.8025	Intermediate Similarity	NPC472950
0.8025	Intermediate Similarity	NPC472952
0.8023	Intermediate Similarity	NPC474156
0.8023	Intermediate Similarity	NPC18953
0.8022	Intermediate Similarity	NPC473503
0.8022	Intermediate Similarity	NPC291203
0.8022	Intermediate Similarity	NPC471464
0.8022	Intermediate Similarity	NPC191915
0.8022	Intermediate Similarity	NPC151214
0.8022	Intermediate Similarity	NPC294686
0.8022	Intermediate Similarity	NPC222731
0.8022	Intermediate Similarity	NPC217205
0.8022	Intermediate Similarity	NPC309866
0.8022	Intermediate Similarity	NPC264101
0.8	Intermediate Similarity	NPC476668
0.8	Intermediate Similarity	NPC473238
0.8	Intermediate Similarity	NPC473066
0.8	Intermediate Similarity	NPC204881
0.8	Intermediate Similarity	NPC473637
0.8	Intermediate Similarity	NPC473830
0.8	Intermediate Similarity	NPC472341
0.7979	Intermediate Similarity	NPC470030
0.7975	Intermediate Similarity	NPC63588
0.7975	Intermediate Similarity	NPC192192
0.7975	Intermediate Similarity	NPC282454
0.7975	Intermediate Similarity	NPC232925
0.7975	Intermediate Similarity	NPC251201
0.7957	Intermediate Similarity	NPC475207
0.7957	Intermediate Similarity	NPC307534
0.7957	Intermediate Similarity	NPC476112
0.7957	Intermediate Similarity	NPC274200
0.7952	Intermediate Similarity	NPC147993
0.7952	Intermediate Similarity	NPC67657
0.7952	Intermediate Similarity	NPC18857
0.7952	Intermediate Similarity	NPC471045
0.7935	Intermediate Similarity	NPC211354
0.7935	Intermediate Similarity	NPC469710
0.7935	Intermediate Similarity	NPC206003
0.7935	Intermediate Similarity	NPC477494
0.7935	Intermediate Similarity	NPC94582
0.7935	Intermediate Similarity	NPC473610
0.7935	Intermediate Similarity	NPC107188
0.7935	Intermediate Similarity	NPC19400
0.7935	Intermediate Similarity	NPC473727
0.7935	Intermediate Similarity	NPC92196
0.7935	Intermediate Similarity	NPC6295

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 NPC470070 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	452
0.1-0.2	4328
0.2-0.3	3119
0.3-0.4	680
0.4-0.5	293
0.5-0.6	204
0.6-0.7	59
0.7-0.8	14
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8415	Intermediate Similarity	NPD6928	Phase 2
0.8111	Intermediate Similarity	NPD8171	Discontinued
0.8077	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1810	Approved
0.747	Intermediate Similarity	NPD1811	Approved
0.7326	Intermediate Similarity	NPD6697	Approved
0.7326	Intermediate Similarity	NPD6115	Approved
0.7326	Intermediate Similarity	NPD6114	Approved
0.7326	Intermediate Similarity	NPD6118	Approved
0.73	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6116	Phase 1
0.7188	Intermediate Similarity	NPD7991	Discontinued
0.7108	Intermediate Similarity	NPD2687	Approved
0.7108	Intermediate Similarity	NPD2686	Approved
0.7108	Intermediate Similarity	NPD2254	Approved
0.7108	Intermediate Similarity	NPD4787	Phase 1
0.7093	Intermediate Similarity	NPD6117	Approved
0.6966	Remote Similarity	NPD7525	Registered
0.686	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.679	Remote Similarity	NPD371	Approved
0.6782	Remote Similarity	NPD3703	Phase 2
0.6739	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3669	Approved
0.6706	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6607	Remote Similarity	NPD7516	Approved
0.6588	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD8294	Approved
0.6549	Remote Similarity	NPD8377	Approved
0.6491	Remote Similarity	NPD8335	Approved
0.6491	Remote Similarity	NPD8380	Approved
0.6491	Remote Similarity	NPD8379	Approved
0.6491	Remote Similarity	NPD8378	Approved
0.6491	Remote Similarity	NPD8033	Approved
0.6491	Remote Similarity	NPD8296	Approved
0.6471	Remote Similarity	NPD5360	Phase 3
0.6471	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD8133	Approved
0.6404	Remote Similarity	NPD6059	Approved
0.6404	Remote Similarity	NPD6054	Approved
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD8035	Phase 2
0.6339	Remote Similarity	NPD6940	Discontinued
0.6322	Remote Similarity	NPD4245	Approved
0.6322	Remote Similarity	NPD4789	Approved
0.6322	Remote Similarity	NPD4244	Approved
0.6296	Remote Similarity	NPD8174	Phase 2
0.6293	Remote Similarity	NPD6370	Approved
0.6289	Remote Similarity	NPD7524	Approved
0.6271	Remote Similarity	NPD7507	Approved
0.6263	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6700	Approved
0.625	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD3702	Approved
0.6207	Remote Similarity	NPD3698	Phase 2
0.6207	Remote Similarity	NPD6016	Approved
0.6207	Remote Similarity	NPD6015	Approved
0.6204	Remote Similarity	NPD6412	Phase 2
0.62	Remote Similarity	NPD6702	Approved
0.62	Remote Similarity	NPD6703	Approved
0.6186	Remote Similarity	NPD7492	Approved
0.617	Remote Similarity	NPD1780	Approved
0.617	Remote Similarity	NPD1779	Approved
0.6167	Remote Similarity	NPD7736	Approved
0.6154	Remote Similarity	NPD5988	Approved
0.6154	Remote Similarity	NPD7638	Approved
0.6146	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6616	Approved
0.6118	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7319	Approved
0.6095	Remote Similarity	NPD7640	Approved
0.6095	Remote Similarity	NPD7639	Approved
0.6091	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD8293	Discontinued
0.6083	Remote Similarity	NPD7078	Approved
0.6068	Remote Similarity	NPD7503	Approved
0.6067	Remote Similarity	NPD4758	Discontinued
0.6067	Remote Similarity	NPD6081	Approved
0.6067	Remote Similarity	NPD5777	Approved
0.6044	Remote Similarity	NPD6942	Approved
0.6044	Remote Similarity	NPD7339	Approved
0.6042	Remote Similarity	NPD6695	Phase 3
0.6038	Remote Similarity	NPD1700	Approved
0.6033	Remote Similarity	NPD6033	Approved
0.6022	Remote Similarity	NPD5364	Discontinued
0.6022	Remote Similarity	NPD3671	Phase 1
0.602	Remote Similarity	NPD8308	Discontinued
0.6	Remote Similarity	NPD6009	Approved
0.5981	Remote Similarity	NPD7632	Discontinued
0.5978	Remote Similarity	NPD6933	Approved
0.5966	Remote Similarity	NPD6067	Discontinued
0.5957	Remote Similarity	NPD7645	Phase 2
0.5943	Remote Similarity	NPD8418	Phase 2
0.5929	Remote Similarity	NPD6882	Approved
0.5909	Remote Similarity	NPD6705	Phase 1
0.5895	Remote Similarity	NPD4748	Discontinued
0.5877	Remote Similarity	NPD4632	Approved
0.5862	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD4224	Phase 2
0.5856	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7320	Approved
0.5825	Remote Similarity	NPD6399	Phase 3
0.5818	Remote Similarity	NPD6675	Approved
0.5818	Remote Similarity	NPD7128	Approved
0.5818	Remote Similarity	NPD5739	Approved
0.5818	Remote Similarity	NPD6402	Approved
0.5806	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.58	Remote Similarity	NPD7750	Discontinued
0.5789	Remote Similarity	NPD8297	Approved
0.5761	Remote Similarity	NPD6926	Approved
0.5761	Remote Similarity	NPD6924	Approved
0.5741	Remote Similarity	NPD4159	Approved
0.5732	Remote Similarity	NPD2267	Suspended
0.5729	Remote Similarity	NPD6931	Approved
0.5729	Remote Similarity	NPD6930	Phase 2
0.5714	Remote Similarity	NPD6899	Approved
0.5714	Remote Similarity	NPD4788	Approved
0.5714	Remote Similarity	NPD6881	Approved
0.5714	Remote Similarity	NPD6686	Approved
0.5714	Remote Similarity	NPD6319	Approved
0.5686	Remote Similarity	NPD5328	Approved
0.5676	Remote Similarity	NPD6008	Approved
0.5673	Remote Similarity	NPD4202	Approved
0.5664	Remote Similarity	NPD6372	Approved
0.5664	Remote Similarity	NPD6373	Approved
0.5657	Remote Similarity	NPD4786	Approved
0.5647	Remote Similarity	NPD1145	Discontinued
0.5625	Remote Similarity	NPD5701	Approved
0.5625	Remote Similarity	NPD6929	Approved
0.5625	Remote Similarity	NPD5697	Approved
0.5614	Remote Similarity	NPD7102	Approved
0.5614	Remote Similarity	NPD4634	Approved
0.5614	Remote Similarity	NPD7290	Approved
0.5614	Remote Similarity	NPD6883	Approved
0.5607	Remote Similarity	NPD7920	Phase 3
0.5607	Remote Similarity	NPD4755	Approved
0.5607	Remote Similarity	NPD7919	Phase 3

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