NPASS Compound

Structure

NPC172823 OpenBabel07101719132D 39 45 0 0 1 0 0 0 0 0999 V2000 4.2351 0.1189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6019 2.7926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4749 2.3560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3196 2.6710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7988 0.0883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0603 2.3010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0336 2.3739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3523 1.6853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8079 1.2159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7585 0.9422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2795 -0.7085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7067 0.2052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2592 0.1043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5104 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7826 0.9276 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6975 1.6584 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4249 0.2567 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3166 -0.8684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3902 1.4510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7712 1.2395 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4655 1.5091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7838 -0.7482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4681 1.1628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6603 1.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3018 1.6951 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0124 1.0407 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7981 0.5618 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5520 0.6933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7810 0.5855 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8800 -1.7413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0273 2.3072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2844 -1.5861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8079 -0.7628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1930 0.4448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4483 -0.2817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4061 0.3926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1099 0.9520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8670 -0.0020 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 1 13 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 6 7 1 0 0 0 0 6 14 2 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 25 1 0 0 0 0 10 13 2 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 27 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 27 1 0 0 0 0 15 10 1 1 0 0 0 15 19 1 0 0 0 0 15 36 1 0 0 0 0 16 24 1 0 0 0 0 16 28 1 6 0 0 0 17 28 1 1 0 0 0 17 37 1 0 0 0 0 18 30 2 0 0 0 0 18 38 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 6 0 0 0 20 25 1 6 0 0 0 20 29 1 0 0 0 0 21 31 2 0 0 0 0 22 32 2 0 0 0 0 22 33 1 0 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 23 34 2 0 0 0 0 24 37 1 0 0 0 0 25 4 1 6 0 0 0 26 5 1 6 0 0 0 26 35 1 0 0 0 0 27 9 1 6 0 0 0 27 39 1 0 0 0 0 28 12 1 6 0 0 0 28 38 1 0 0 0 0 29 21 1 1 0 0 0 29 36 1 0 0 0 0 29 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.22
Volume:	522.328
LogP:	2.376
LogD:	1.141
LogS:	-4.086
# Rotatable Bonds:	2
TPSA:	145.66
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.301
Synthetic Accessibility Score:	7.655
Fsp3:	0.724
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:	-5.54
MDCK Permeability:	2.834873703250196e-05
Pgp-inhibitor:	0.892
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.588
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.746
Plasma Protein Binding (PPB):	33.4277229309082%
Volume Distribution (VD):	0.564
Pgp-substrate:	39.7898063659668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.979
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.217
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.47
CYP3A4-substrate:	0.339

ADMET: Excretion

Clearance (CL):	11.143
Half-life (T1/2):	0.261

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.492
Drug-inuced Liver Injury (DILI):	0.892
AMES Toxicity:	0.893
Rat Oral Acute Toxicity:	0.922
Maximum Recommended Daily Dose:	0.421
Skin Sensitization:	0.662
Carcinogencity:	0.82
Eye Corrosion:	0.036
Eye Irritation:	0.012
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC172823

Natural Product ID:	NPC172823
*Common Name:**	Schirubridilactone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GBIGSKNEWMRPTE-HLVFYAQTSA-N
Standard InCHI:	InChI=1S/C29H34O10/c1-13(22(32)33)10-15-19-20-25(4,23(34)26(19,5)35)8-9-27-12-28-16(24(2,3)37-17(28)11-18(30)38-28)7-6-14(27)21(31)29(20,36-15)39-27/h6,10,15-17,19-20,35H,7-9,11-12H2,1-5H3,(H,32,33)/b13-10-/t15-,16+,17-,19-,20+,25+,26-,27+,28-,29+/m1/s1
SMILES:	C/C(=C/[C@@H]1[C@@H]2[C@H]3[C@](C)(CC[C@]45C[C@@]67[C@@H](CC=C4C(=O)[C@@]3(O1)O5)C(C)(C)O[C@@H]6CC(=O)O7)C(=O)[C@]2(C)O)/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076669
PubChem CID:	46186627
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[16494492]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16494492]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[17190445]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17489633]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[20146529]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24804	Schisandra rubriflora	Species	Schisandraceae	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
EC50	1
IC50	2
Others	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[478607]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[478607]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	15.2	ug.mL-1	PMID[478607]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Selectivity Index	=	9.0	n.a.	PMID[478607]

☑ 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 NPC172823 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	361
0.1-0.2	2251
0.2-0.3	7013
0.3-0.4	13278
0.4-0.5	11790
0.5-0.6	6134
0.6-0.7	1690
0.7-0.8	165
0.8-0.85	4
0.85-0.9	5
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9504	High Similarity	NPC469351
0.9492	High Similarity	NPC42747
0.9417	High Similarity	NPC11732
0.935	High Similarity	NPC224623
0.9262	High Similarity	NPC13071
0.9244	High Similarity	NPC192309
0.9167	High Similarity	NPC1538
0.8934	High Similarity	NPC144625
0.8917	High Similarity	NPC163693
0.8917	High Similarity	NPC147635
0.8852	High Similarity	NPC186339
0.7967	Intermediate Similarity	NPC209058
0.7937	Intermediate Similarity	NPC477092
0.792	Intermediate Similarity	NPC475305
0.792	Intermediate Similarity	NPC36754
0.792	Intermediate Similarity	NPC471145
0.7886	Intermediate Similarity	NPC471570
0.7869	Intermediate Similarity	NPC477103
0.7857	Intermediate Similarity	NPC475401
0.7857	Intermediate Similarity	NPC161060
0.784	Intermediate Similarity	NPC277583
0.7829	Intermediate Similarity	NPC129992
0.7815	Intermediate Similarity	NPC472755
0.7812	Intermediate Similarity	NPC473228
0.7812	Intermediate Similarity	NPC470829
0.7805	Intermediate Similarity	NPC474750
0.7805	Intermediate Similarity	NPC475495
0.7803	Intermediate Similarity	NPC472770
0.7787	Intermediate Similarity	NPC217041
0.7787	Intermediate Similarity	NPC477102
0.7778	Intermediate Similarity	NPC471146
0.7769	Intermediate Similarity	NPC26617
0.775	Intermediate Similarity	NPC472756
0.775	Intermediate Similarity	NPC100487
0.7742	Intermediate Similarity	NPC473522
0.7742	Intermediate Similarity	NPC475277
0.7742	Intermediate Similarity	NPC477093
0.7731	Intermediate Similarity	NPC105725
0.7724	Intermediate Similarity	NPC471884
0.7724	Intermediate Similarity	NPC182185
0.7724	Intermediate Similarity	NPC257240
0.7705	Intermediate Similarity	NPC220773
0.7705	Intermediate Similarity	NPC278693
0.7705	Intermediate Similarity	NPC117604
0.7704	Intermediate Similarity	NPC471234
0.7698	Intermediate Similarity	NPC54739
0.7687	Intermediate Similarity	NPC472769
0.7686	Intermediate Similarity	NPC469441
0.7686	Intermediate Similarity	NPC41674
0.7686	Intermediate Similarity	NPC228311
0.7674	Intermediate Similarity	NPC472001
0.7661	Intermediate Similarity	NPC287311
0.7647	Intermediate Similarity	NPC171759
0.7623	Intermediate Similarity	NPC470192
0.7623	Intermediate Similarity	NPC290247
0.7623	Intermediate Similarity	NPC469787
0.7623	Intermediate Similarity	NPC469788
0.7619	Intermediate Similarity	NPC471380
0.76	Intermediate Similarity	NPC98870
0.7583	Intermediate Similarity	NPC49393
0.7583	Intermediate Similarity	NPC472754
0.7578	Intermediate Similarity	NPC475372
0.7578	Intermediate Similarity	NPC13710
0.7563	Intermediate Similarity	NPC280963
0.7561	Intermediate Similarity	NPC10150
0.7561	Intermediate Similarity	NPC329876
0.7557	Intermediate Similarity	NPC472768
0.7542	Intermediate Similarity	NPC108475
0.7542	Intermediate Similarity	NPC170143
0.7542	Intermediate Similarity	NPC213947
0.7541	Intermediate Similarity	NPC168890
0.7541	Intermediate Similarity	NPC223450
0.7541	Intermediate Similarity	NPC472751
0.7541	Intermediate Similarity	NPC472749
0.754	Intermediate Similarity	NPC46269
0.754	Intermediate Similarity	NPC106395
0.7538	Intermediate Similarity	NPC472000
0.7538	Intermediate Similarity	NPC471999
0.7521	Intermediate Similarity	NPC475873
0.7521	Intermediate Similarity	NPC67584
0.7521	Intermediate Similarity	NPC475871
0.7521	Intermediate Similarity	NPC475945
0.7519	Intermediate Similarity	NPC312536
0.75	Intermediate Similarity	NPC15993
0.75	Intermediate Similarity	NPC187876
0.75	Intermediate Similarity	NPC128733
0.75	Intermediate Similarity	NPC475588
0.75	Intermediate Similarity	NPC472753
0.75	Intermediate Similarity	NPC150923
0.75	Intermediate Similarity	NPC133907
0.75	Intermediate Similarity	NPC474742
0.75	Intermediate Similarity	NPC185141
0.75	Intermediate Similarity	NPC46998
0.75	Intermediate Similarity	NPC110443
0.748	Intermediate Similarity	NPC138303
0.748	Intermediate Similarity	NPC67290
0.748	Intermediate Similarity	NPC133677
0.748	Intermediate Similarity	NPC176756
0.748	Intermediate Similarity	NPC471382
0.7479	Intermediate Similarity	NPC470188
0.746	Intermediate Similarity	NPC138757
0.746	Intermediate Similarity	NPC123855
0.746	Intermediate Similarity	NPC76550
0.7459	Intermediate Similarity	NPC474741
0.7459	Intermediate Similarity	NPC472748
0.7459	Intermediate Similarity	NPC203659
0.7458	Intermediate Similarity	NPC213078
0.7447	Intermediate Similarity	NPC470426
0.7442	Intermediate Similarity	NPC475309
0.7438	Intermediate Similarity	NPC149371
0.7438	Intermediate Similarity	NPC324017
0.7438	Intermediate Similarity	NPC118405
0.7438	Intermediate Similarity	NPC474747
0.7438	Intermediate Similarity	NPC86077
0.7438	Intermediate Similarity	NPC320019
0.7438	Intermediate Similarity	NPC471757
0.7438	Intermediate Similarity	NPC78127
0.7424	Intermediate Similarity	NPC472399
0.7419	Intermediate Similarity	NPC167044
0.7419	Intermediate Similarity	NPC475960
0.7419	Intermediate Similarity	NPC308191
0.7398	Intermediate Similarity	NPC314244
0.7398	Intermediate Similarity	NPC291643
0.7398	Intermediate Similarity	NPC469401
0.7398	Intermediate Similarity	NPC243998
0.7398	Intermediate Similarity	NPC179891
0.7395	Intermediate Similarity	NPC161493
0.7394	Intermediate Similarity	NPC471171
0.7377	Intermediate Similarity	NPC124881
0.7377	Intermediate Similarity	NPC472750
0.7377	Intermediate Similarity	NPC110989
0.7377	Intermediate Similarity	NPC469350
0.7377	Intermediate Similarity	NPC472747
0.7376	Intermediate Similarity	NPC25887
0.7373	Intermediate Similarity	NPC163228
0.7373	Intermediate Similarity	NPC52044
0.7372	Intermediate Similarity	NPC88668
0.7364	Intermediate Similarity	NPC475323
0.7364	Intermediate Similarity	NPC473656
0.7355	Intermediate Similarity	NPC477950
0.7355	Intermediate Similarity	NPC162024
0.7355	Intermediate Similarity	NPC47880
0.7355	Intermediate Similarity	NPC476270
0.7353	Intermediate Similarity	NPC213634
0.7353	Intermediate Similarity	NPC476852
0.7353	Intermediate Similarity	NPC476855
0.7333	Intermediate Similarity	NPC54843
0.7333	Intermediate Similarity	NPC471610
0.7333	Intermediate Similarity	NPC221615
0.7317	Intermediate Similarity	NPC309190
0.7311	Intermediate Similarity	NPC126156
0.7311	Intermediate Similarity	NPC142529
0.7311	Intermediate Similarity	NPC91771
0.7308	Intermediate Similarity	NPC288679
0.7305	Intermediate Similarity	NPC476825
0.7295	Intermediate Similarity	NPC225353
0.7295	Intermediate Similarity	NPC66110
0.7293	Intermediate Similarity	NPC471392
0.7293	Intermediate Similarity	NPC469352
0.7292	Intermediate Similarity	NPC194854
0.7292	Intermediate Similarity	NPC48813
0.7288	Intermediate Similarity	NPC127019
0.7279	Intermediate Similarity	NPC470851
0.7279	Intermediate Similarity	NPC475371
0.7279	Intermediate Similarity	NPC476851
0.7279	Intermediate Similarity	NPC476854
0.7273	Intermediate Similarity	NPC472401
0.7265	Intermediate Similarity	NPC221282
0.7259	Intermediate Similarity	NPC42399
0.7259	Intermediate Similarity	NPC287423
0.7258	Intermediate Similarity	NPC475217
0.7258	Intermediate Similarity	NPC475802
0.7258	Intermediate Similarity	NPC190867
0.7258	Intermediate Similarity	NPC54737
0.7258	Intermediate Similarity	NPC252234
0.7252	Intermediate Similarity	NPC9674
0.7252	Intermediate Similarity	NPC472933
0.7252	Intermediate Similarity	NPC19028
0.725	Intermediate Similarity	NPC477949
0.725	Intermediate Similarity	NPC474313
0.7246	Intermediate Similarity	NPC168879
0.7241	Intermediate Similarity	NPC475462
0.7241	Intermediate Similarity	NPC16729
0.7239	Intermediate Similarity	NPC470922
0.7231	Intermediate Similarity	NPC239273
0.7227	Intermediate Similarity	NPC469873
0.7227	Intermediate Similarity	NPC475900
0.7227	Intermediate Similarity	NPC36954
0.7227	Intermediate Similarity	NPC170120
0.7227	Intermediate Similarity	NPC213698
0.7226	Intermediate Similarity	NPC475389
0.7226	Intermediate Similarity	NPC473838
0.7222	Intermediate Similarity	NPC38154
0.7222	Intermediate Similarity	NPC47951
0.7222	Intermediate Similarity	NPC139838
0.7222	Intermediate Similarity	NPC59489
0.7218	Intermediate Similarity	NPC19464
0.7214	Intermediate Similarity	NPC243014
0.7213	Intermediate Similarity	NPC201718
0.7213	Intermediate Similarity	NPC475099

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 NPC172823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	2786
0.2-0.3	3897
0.3-0.4	1463
0.4-0.5	377
0.5-0.6	200
0.6-0.7	28
0.7-0.8	3
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
0.7769	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6371	Approved
0.7259	Intermediate Similarity	NPD7078	Approved
0.7239	Intermediate Similarity	NPD7492	Approved
0.7197	Intermediate Similarity	NPD6054	Approved
0.7185	Intermediate Similarity	NPD6616	Approved
0.7177	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6370	Approved
0.708	Intermediate Similarity	NPD7736	Approved
0.7068	Intermediate Similarity	NPD6059	Approved
0.7015	Intermediate Similarity	NPD6016	Approved
0.7015	Intermediate Similarity	NPD6015	Approved
0.7007	Intermediate Similarity	NPD8293	Discontinued
0.6963	Remote Similarity	NPD5988	Approved
0.6942	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7319	Approved
0.6891	Remote Similarity	NPD5785	Approved
0.6815	Remote Similarity	NPD6319	Approved
0.6812	Remote Similarity	NPD7507	Approved
0.6794	Remote Similarity	NPD6882	Approved
0.6794	Remote Similarity	NPD6053	Discontinued
0.6716	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6615	Remote Similarity	NPD6686	Approved
0.6596	Remote Similarity	NPD6033	Approved
0.6591	Remote Similarity	NPD6649	Approved
0.6591	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6650	Approved
0.6585	Remote Similarity	NPD5282	Discontinued
0.6565	Remote Similarity	NPD6373	Approved
0.6565	Remote Similarity	NPD6372	Approved
0.6529	Remote Similarity	NPD1695	Approved
0.6508	Remote Similarity	NPD5696	Approved
0.6489	Remote Similarity	NPD6881	Approved
0.6489	Remote Similarity	NPD6899	Approved
0.6489	Remote Similarity	NPD7320	Approved
0.6471	Remote Similarity	NPD7115	Discovery
0.6471	Remote Similarity	NPD5363	Approved
0.6463	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5739	Approved
0.6462	Remote Similarity	NPD6675	Approved
0.6462	Remote Similarity	NPD7128	Approved
0.6462	Remote Similarity	NPD6402	Approved
0.6458	Remote Similarity	NPD7260	Phase 2
0.6423	Remote Similarity	NPD7983	Approved
0.6417	Remote Similarity	NPD5786	Approved
0.6414	Remote Similarity	NPD6845	Suspended
0.6412	Remote Similarity	NPD5697	Approved
0.6403	Remote Similarity	NPD8267	Approved
0.6403	Remote Similarity	NPD8516	Approved
0.6403	Remote Similarity	NPD8268	Approved
0.6403	Remote Similarity	NPD8266	Approved
0.6403	Remote Similarity	NPD8515	Approved
0.6403	Remote Similarity	NPD8513	Phase 3
0.6403	Remote Similarity	NPD8269	Approved
0.6403	Remote Similarity	NPD8517	Approved
0.6391	Remote Similarity	NPD7290	Approved
0.6391	Remote Similarity	NPD7102	Approved
0.6391	Remote Similarity	NPD6883	Approved
0.6389	Remote Similarity	NPD5956	Approved
0.6378	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.637	Remote Similarity	NPD4632	Approved
0.6343	Remote Similarity	NPD6847	Approved
0.6343	Remote Similarity	NPD6869	Approved
0.6343	Remote Similarity	NPD6617	Approved
0.6343	Remote Similarity	NPD8130	Phase 1
0.6341	Remote Similarity	NPD46	Approved
0.6341	Remote Similarity	NPD6698	Approved
0.6336	Remote Similarity	NPD6008	Approved
0.6316	Remote Similarity	NPD6012	Approved
0.6316	Remote Similarity	NPD6014	Approved
0.6316	Remote Similarity	NPD6013	Approved
0.6312	Remote Similarity	NPD7604	Phase 2
0.6312	Remote Similarity	NPD8328	Phase 3
0.6304	Remote Similarity	NPD7328	Approved
0.6304	Remote Similarity	NPD7327	Approved
0.6299	Remote Similarity	NPD6083	Phase 2
0.6299	Remote Similarity	NPD6084	Phase 2
0.6288	Remote Similarity	NPD6412	Phase 2
0.6288	Remote Similarity	NPD5701	Approved
0.6286	Remote Similarity	NPD5983	Phase 2
0.6286	Remote Similarity	NPD8033	Approved
0.627	Remote Similarity	NPD5695	Phase 3
0.6259	Remote Similarity	NPD7516	Approved
0.625	Remote Similarity	NPD4225	Approved
0.6241	Remote Similarity	NPD6011	Approved
0.623	Remote Similarity	NPD4250	Approved
0.623	Remote Similarity	NPD4251	Approved
0.6224	Remote Similarity	NPD6336	Discontinued
0.6218	Remote Similarity	NPD4269	Approved
0.6218	Remote Similarity	NPD4270	Approved
0.6214	Remote Similarity	NPD8377	Approved
0.6214	Remote Similarity	NPD8294	Approved
0.6198	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD8074	Phase 3
0.617	Remote Similarity	NPD8335	Approved
0.617	Remote Similarity	NPD8379	Approved
0.617	Remote Similarity	NPD8378	Approved
0.617	Remote Similarity	NPD7503	Approved
0.617	Remote Similarity	NPD8296	Approved
0.617	Remote Similarity	NPD8380	Approved
0.6167	Remote Similarity	NPD5362	Discontinued
0.6148	Remote Similarity	NPD4249	Approved
0.6148	Remote Similarity	NPD4634	Approved
0.6134	Remote Similarity	NPD5369	Approved
0.6107	Remote Similarity	NPD5211	Phase 2
0.6103	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD7642	Approved
0.6083	Remote Similarity	NPD6435	Approved
0.608	Remote Similarity	NPD7838	Discovery
0.6077	Remote Similarity	NPD7639	Approved
0.6077	Remote Similarity	NPD7640	Approved
0.6066	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.605	Remote Similarity	NPD4252	Approved
0.6043	Remote Similarity	NPD6274	Approved
0.6032	Remote Similarity	NPD5693	Phase 1
0.6031	Remote Similarity	NPD1700	Approved
0.6028	Remote Similarity	NPD7101	Approved
0.6028	Remote Similarity	NPD7100	Approved
0.6027	Remote Similarity	NPD8336	Approved
0.6027	Remote Similarity	NPD8337	Approved
0.6023	Remote Similarity	NPD7799	Discontinued
0.6016	Remote Similarity	NPD4629	Approved
0.6016	Remote Similarity	NPD5210	Approved
0.6015	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD5779	Approved
0.5984	Remote Similarity	NPD5778	Approved
0.5969	Remote Similarity	NPD7839	Suspended
0.5957	Remote Similarity	NPD6335	Approved
0.5954	Remote Similarity	NPD5285	Approved
0.5954	Remote Similarity	NPD5286	Approved
0.5954	Remote Similarity	NPD4696	Approved
0.5944	Remote Similarity	NPD8444	Approved
0.5944	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD4755	Approved
0.5917	Remote Similarity	NPD4821	Approved
0.5917	Remote Similarity	NPD4820	Approved
0.5917	Remote Similarity	NPD4819	Approved
0.5917	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD4822	Approved
0.5917	Remote Similarity	NPD5368	Approved
0.5906	Remote Similarity	NPD7637	Suspended
0.5903	Remote Similarity	NPD8080	Discontinued
0.5899	Remote Similarity	NPD8133	Approved
0.5887	Remote Similarity	NPD6317	Approved
0.5882	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD6904	Approved
0.5873	Remote Similarity	NPD6080	Approved
0.5873	Remote Similarity	NPD6673	Approved
0.5868	Remote Similarity	NPD4790	Discontinued
0.5867	Remote Similarity	NPD8338	Approved
0.5865	Remote Similarity	NPD4633	Approved
0.5865	Remote Similarity	NPD5224	Approved
0.5865	Remote Similarity	NPD5225	Approved
0.5865	Remote Similarity	NPD5226	Approved
0.5862	Remote Similarity	NPD7830	Approved
0.5862	Remote Similarity	NPD7829	Approved
0.5859	Remote Similarity	NPD6399	Phase 3
0.5845	Remote Similarity	NPD6313	Approved
0.5845	Remote Similarity	NPD6314	Approved
0.5833	Remote Similarity	NPD6909	Approved
0.5833	Remote Similarity	NPD6908	Approved
0.5833	Remote Similarity	NPD4700	Approved
0.5821	Remote Similarity	NPD5174	Approved
0.5821	Remote Similarity	NPD5175	Approved
0.5797	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5737	Approved
0.5794	Remote Similarity	NPD6672	Approved
0.5789	Remote Similarity	NPD5223	Approved
0.5789	Remote Similarity	NPD5344	Discontinued
0.5782	Remote Similarity	NPD8451	Approved
0.5781	Remote Similarity	NPD6050	Approved
0.5772	Remote Similarity	NPD7154	Phase 3
0.5772	Remote Similarity	NPD5332	Approved
0.5772	Remote Similarity	NPD5331	Approved
0.5769	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD4730	Approved
0.5766	Remote Similarity	NPD4729	Approved
0.5753	Remote Similarity	NPD6067	Discontinued
0.575	Remote Similarity	NPD4268	Approved
0.575	Remote Similarity	NPD4271	Approved
0.5748	Remote Similarity	NPD4753	Phase 2
0.5743	Remote Similarity	NPD8448	Approved
0.5735	Remote Similarity	NPD4768	Approved
0.5735	Remote Similarity	NPD4767	Approved
0.5734	Remote Similarity	NPD7641	Discontinued
0.5724	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8341	Approved
0.5714	Remote Similarity	NPD8340	Approved
0.5714	Remote Similarity	NPD8299	Approved
0.5714	Remote Similarity	NPD6648	Approved
0.5714	Remote Similarity	NPD8342	Approved
0.5703	Remote Similarity	NPD5692	Phase 3
0.5693	Remote Similarity	NPD6614	Approved
0.5691	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD5209	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