NPASS Compound

Structure

NPC475561 OpenBabel07101719132D 44 52 0 0 1 0 0 0 0 0999 V2000 -0.1229 3.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1926 -2.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5945 -3.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 3.4344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5227 1.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5227 0.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6567 1.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6567 -0.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7907 1.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3266 0.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4606 -0.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7285 -1.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0649 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8625 -1.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4716 -2.3612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 0.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3266 -2.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8625 -3.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0796 2.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 -1.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7907 0.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1926 -0.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4606 -1.0303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5945 -1.5303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0704 -1.5522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3266 -1.5303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9247 -0.0303 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4606 -3.0303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 2.1473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1926 -1.0303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5945 -2.5303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8625 -2.5303 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7285 -3.0303 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4606 -4.0303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.4563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9247 -1.0303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4863 1.3383 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 3 35 1 0 0 0 0 4 41 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 23 2 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 24 2 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 15 1 0 0 0 0 13 28 1 0 0 0 0 14 36 1 0 0 0 0 16 24 1 0 0 0 0 16 30 1 0 0 0 0 17 29 1 0 0 0 0 17 31 1 0 0 0 0 18 26 2 0 0 0 0 19 33 1 0 0 0 0 19 38 1 0 0 0 0 20 36 1 0 0 0 0 20 37 1 0 0 0 0 21 33 1 0 0 0 0 21 43 1 0 0 0 0 22 34 1 0 0 0 0 22 42 1 0 0 0 0 24 34 1 0 0 0 0 25 11 1 1 0 0 0 25 27 1 0 0 0 0 25 29 1 0 0 0 0 26 28 1 0 0 0 0 26 32 1 0 0 0 0 27 35 1 6 0 0 0 28 36 1 6 0 0 0 29 34 1 6 0 0 0 30 23 1 1 0 0 0 30 42 1 0 0 0 0 31 35 1 1 0 0 0 31 39 1 0 0 0 0 32 40 2 0 0 0 0 32 44 1 0 0 0 0 33 1 1 6 0 0 0 33 41 1 0 0 0 0 34 2 1 1 0 0 0 35 37 1 1 0 0 0 36 37 1 1 0 0 0 37 15 1 6 0 0 0 38 18 1 6 0 0 0 38 43 1 0 0 0 0 38 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	600.35
Volume:	625.718
LogP:	5.308
LogD:	3.972
LogS:	-5.215
# Rotatable Bonds:	3
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.308
Synthetic Accessibility Score:	6.125
Fsp3:	0.711
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.195
MDCK Permeability:	3.199735510861501e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.136

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	97.19864654541016%
Volume Distribution (VD):	1.101
Pgp-substrate:	1.6205757856369019%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.756
CYP2C19-inhibitor:	0.469
CYP2C19-substrate:	0.896
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.337
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.972
CYP3A4-substrate:	0.893

ADMET: Excretion

Clearance (CL):	7.368
Half-life (T1/2):	0.375

ADMET: Toxicity

hERG Blockers:	0.928
Human Hepatotoxicity (H-HT):	0.528
Drug-inuced Liver Injury (DILI):	0.109
AMES Toxicity:	0.491
Rat Oral Acute Toxicity:	0.516
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.964
Carcinogencity:	0.14
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC475561

Natural Product ID:	NPC475561
*Common Name:**	Acutissimatriterpene D
IUPAC Name:	n.a.
Synonyms:	Acutissimatriterpene D
Standard InCHIKey:	HTAWBNJTNNTCSA-ZOMIBVFZSA-N
Standard InCHI:	InChI=1S/C38H48O6/c1-33(41-4)19-38(43-21-33)18-26(32(40)44-38)28-13-15-37-20-36(28,37)14-12-27-25-11-10-24-16-30(23-8-6-5-7-9-23)42-22-34(24,2)29(25)17-31(39)35(27,37)3/h5-10,18,25,27-31,39H,11-17,19-22H2,1-4H3/t25-,27-,28+,29-,30+,31-,33-,34+,35+,36-,37-,38+/m1/s1
SMILES:	CC1(CC2(C=C(C(=O)O2)C3CCC45C3(C4)CCC6C5(C(CC7C6CC=C8C7(COC(C8)C9=CC=CC=C9)C)O)C)OC1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508201
PubChem CID:	44560355
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO33358	phyllanthus acutissima	Species	n.a.	Eukaryota	aerial parts	n.a.	n.a.	PMID[18271551]

☑ 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
ED50	6
IC50	1
Others	2

Activity Type	# Activity
Cell Line	5
Individual Protein	1
NON-MOLECULAR	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	37.8	%	PMID[549492]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[549492]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[549492]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[549492]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[549492]
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[549492]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Ratio IC50/EC50	=	2.5	n.a.	PMID[549492]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	5.1	ug.mL-1	PMID[549492]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	12.9	ug.mL-1	PMID[549492]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	5.0	ug ml-1	PMID[549492]

☑ 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 NPC475561 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	339
0.1-0.2	1159
0.2-0.3	2483
0.3-0.4	4823
0.4-0.5	9242
0.5-0.6	16959
0.6-0.7	6458
0.7-0.8	1034
0.8-0.85	180
0.85-0.9	15
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475417
0.9122	High Similarity	NPC472658
0.9122	High Similarity	NPC472657
0.8944	High Similarity	NPC262324
0.8819	High Similarity	NPC79921
0.8811	High Similarity	NPC243893
0.8759	High Similarity	NPC471862
0.8758	High Similarity	NPC476784
0.8699	High Similarity	NPC471856
0.8696	High Similarity	NPC475197
0.8696	High Similarity	NPC473467
0.8671	High Similarity	NPC471864
0.8608	High Similarity	NPC471861
0.8581	High Similarity	NPC323356
0.8581	High Similarity	NPC471138
0.8581	High Similarity	NPC326328
0.8581	High Similarity	NPC309991
0.8571	High Similarity	NPC322048
0.8571	High Similarity	NPC318447
0.8543	High Similarity	NPC469448
0.8514	High Similarity	NPC91703
0.8506	High Similarity	NPC326235
0.8506	High Similarity	NPC475548
0.8506	High Similarity	NPC290683
0.8506	High Similarity	NPC475638
0.8506	High Similarity	NPC323001
0.8503	High Similarity	NPC224491
0.8497	Intermediate Similarity	NPC471135
0.8487	Intermediate Similarity	NPC478123
0.8472	Intermediate Similarity	NPC48929
0.8467	Intermediate Similarity	NPC473602
0.8456	Intermediate Similarity	NPC475122
0.8442	Intermediate Similarity	NPC34066
0.8435	Intermediate Similarity	NPC275592
0.8435	Intermediate Similarity	NPC90614
0.8435	Intermediate Similarity	NPC472547
0.8435	Intermediate Similarity	NPC100913
0.8431	Intermediate Similarity	NPC472548
0.8428	Intermediate Similarity	NPC475567
0.8428	Intermediate Similarity	NPC473557
0.8428	Intermediate Similarity	NPC473468
0.8428	Intermediate Similarity	NPC477491
0.8425	Intermediate Similarity	NPC39549
0.8421	Intermediate Similarity	NPC476173
0.84	Intermediate Similarity	NPC469349
0.84	Intermediate Similarity	NPC171525
0.84	Intermediate Similarity	NPC472572
0.84	Intermediate Similarity	NPC29704
0.84	Intermediate Similarity	NPC470159
0.84	Intermediate Similarity	NPC472556
0.84	Intermediate Similarity	NPC472575
0.84	Intermediate Similarity	NPC158663
0.84	Intermediate Similarity	NPC96903
0.84	Intermediate Similarity	NPC200471
0.84	Intermediate Similarity	NPC470157
0.84	Intermediate Similarity	NPC184817
0.84	Intermediate Similarity	NPC70403
0.84	Intermediate Similarity	NPC177940
0.84	Intermediate Similarity	NPC174982
0.84	Intermediate Similarity	NPC472568
0.84	Intermediate Similarity	NPC473088
0.84	Intermediate Similarity	NPC472571
0.84	Intermediate Similarity	NPC471104
0.84	Intermediate Similarity	NPC476973
0.8389	Intermediate Similarity	NPC163087
0.8389	Intermediate Similarity	NPC131966
0.8389	Intermediate Similarity	NPC191387
0.8378	Intermediate Similarity	NPC87448
0.8378	Intermediate Similarity	NPC291599
0.8378	Intermediate Similarity	NPC41481
0.8378	Intermediate Similarity	NPC97947
0.8378	Intermediate Similarity	NPC472576
0.8378	Intermediate Similarity	NPC16912
0.8378	Intermediate Similarity	NPC118080
0.8378	Intermediate Similarity	NPC27377
0.8375	Intermediate Similarity	NPC475175
0.8375	Intermediate Similarity	NPC475531
0.8375	Intermediate Similarity	NPC475198
0.8366	Intermediate Similarity	NPC62792
0.8365	Intermediate Similarity	NPC471858
0.8356	Intermediate Similarity	NPC472551
0.8356	Intermediate Similarity	NPC472545
0.8355	Intermediate Similarity	NPC301556
0.8355	Intermediate Similarity	NPC92293
0.8355	Intermediate Similarity	NPC471101
0.8355	Intermediate Similarity	NPC270590
0.8355	Intermediate Similarity	NPC266265
0.8354	Intermediate Similarity	NPC478124
0.8345	Intermediate Similarity	NPC203486
0.8344	Intermediate Similarity	NPC474935
0.8344	Intermediate Similarity	NPC477623
0.8333	Intermediate Similarity	NPC25768
0.8333	Intermediate Similarity	NPC472569
0.8333	Intermediate Similarity	NPC95810
0.8333	Intermediate Similarity	NPC472573
0.8333	Intermediate Similarity	NPC95265
0.8333	Intermediate Similarity	NPC475759
0.8333	Intermediate Similarity	NPC470152
0.8333	Intermediate Similarity	NPC57628
0.8333	Intermediate Similarity	NPC163719
0.8333	Intermediate Similarity	NPC188865
0.8333	Intermediate Similarity	NPC70716
0.8333	Intermediate Similarity	NPC241951
0.8333	Intermediate Similarity	NPC125106
0.8333	Intermediate Similarity	NPC472570
0.8333	Intermediate Similarity	NPC471139
0.8333	Intermediate Similarity	NPC476974
0.8333	Intermediate Similarity	NPC11685
0.8323	Intermediate Similarity	NPC472549
0.8323	Intermediate Similarity	NPC471176
0.8323	Intermediate Similarity	NPC469422
0.8322	Intermediate Similarity	NPC475513
0.8322	Intermediate Similarity	NPC473755
0.8313	Intermediate Similarity	NPC471850
0.8312	Intermediate Similarity	NPC477905
0.8311	Intermediate Similarity	NPC171207
0.8311	Intermediate Similarity	NPC97667
0.8311	Intermediate Similarity	NPC475400
0.8302	Intermediate Similarity	NPC478073
0.8302	Intermediate Similarity	NPC478125
0.8289	Intermediate Similarity	NPC281717
0.8288	Intermediate Similarity	NPC473399
0.8288	Intermediate Similarity	NPC473216
0.828	Intermediate Similarity	NPC319404
0.8272	Intermediate Similarity	NPC477488
0.8264	Intermediate Similarity	NPC470278
0.8247	Intermediate Similarity	NPC298072
0.8247	Intermediate Similarity	NPC469415
0.8243	Intermediate Similarity	NPC214550
0.8243	Intermediate Similarity	NPC475652
0.8243	Intermediate Similarity	NPC210591
0.8239	Intermediate Similarity	NPC275477
0.8235	Intermediate Similarity	NPC473215
0.8235	Intermediate Similarity	NPC476975
0.8231	Intermediate Similarity	NPC472374
0.8231	Intermediate Similarity	NPC472372
0.8224	Intermediate Similarity	NPC478263
0.8221	Intermediate Similarity	NPC471859
0.8221	Intermediate Similarity	NPC471860
0.8219	Intermediate Similarity	NPC474608
0.8217	Intermediate Similarity	NPC469417
0.8212	Intermediate Similarity	NPC111466
0.821	Intermediate Similarity	NPC40138
0.8207	Intermediate Similarity	NPC475493
0.8205	Intermediate Similarity	NPC469456
0.8205	Intermediate Similarity	NPC469398
0.82	Intermediate Similarity	NPC34012
0.82	Intermediate Similarity	NPC472546
0.8194	Intermediate Similarity	NPC147561
0.8194	Intermediate Similarity	NPC475138
0.8193	Intermediate Similarity	NPC475244
0.8188	Intermediate Similarity	NPC211137
0.8188	Intermediate Similarity	NPC473109
0.8188	Intermediate Similarity	NPC473081
0.8188	Intermediate Similarity	NPC473060
0.8188	Intermediate Similarity	NPC473085
0.8188	Intermediate Similarity	NPC184747
0.8188	Intermediate Similarity	NPC473112
0.8188	Intermediate Similarity	NPC476094
0.8188	Intermediate Similarity	NPC477904
0.8188	Intermediate Similarity	NPC4341
0.8188	Intermediate Similarity	NPC48017
0.8188	Intermediate Similarity	NPC200592
0.8188	Intermediate Similarity	NPC43241
0.8188	Intermediate Similarity	NPC473613
0.8188	Intermediate Similarity	NPC147880
0.8188	Intermediate Similarity	NPC183270
0.8188	Intermediate Similarity	NPC473758
0.8187	Intermediate Similarity	NPC329960
0.8187	Intermediate Similarity	NPC295408
0.8187	Intermediate Similarity	NPC150893
0.8182	Intermediate Similarity	NPC470245
0.8182	Intermediate Similarity	NPC473214
0.8182	Intermediate Similarity	NPC303429
0.8182	Intermediate Similarity	NPC222102
0.8176	Intermediate Similarity	NPC475373
0.8176	Intermediate Similarity	NPC183122
0.8176	Intermediate Similarity	NPC283375
0.8165	Intermediate Similarity	NPC469399
0.8165	Intermediate Similarity	NPC49297
0.8163	Intermediate Similarity	NPC291638
0.8163	Intermediate Similarity	NPC472577
0.8163	Intermediate Similarity	NPC66761
0.8163	Intermediate Similarity	NPC17877
0.8163	Intermediate Similarity	NPC195647
0.8158	Intermediate Similarity	NPC40085
0.8158	Intermediate Similarity	NPC264270
0.8158	Intermediate Similarity	NPC478264
0.8146	Intermediate Similarity	NPC473673
0.8146	Intermediate Similarity	NPC270498
0.8146	Intermediate Similarity	NPC246480
0.8146	Intermediate Similarity	NPC177340
0.8146	Intermediate Similarity	NPC147217
0.8146	Intermediate Similarity	NPC475429
0.8146	Intermediate Similarity	NPC191082
0.8146	Intermediate Similarity	NPC139067
0.8146	Intermediate Similarity	NPC477894
0.8141	Intermediate Similarity	NPC261659
0.8138	Intermediate Similarity	NPC72915
0.8133	Intermediate Similarity	NPC266374

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 NPC475561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	745
0.2-0.3	1633
0.3-0.4	3107
0.4-0.5	2237
0.5-0.6	952
0.6-0.7	183
0.7-0.8	14
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
0.8221	Intermediate Similarity	NPD7799	Discontinued
0.8039	Intermediate Similarity	NPD7236	Approved
0.7785	Intermediate Similarity	NPD7239	Suspended
0.7703	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8127	Discontinued
0.7483	Intermediate Similarity	NPD7741	Discontinued
0.7434	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5125	Phase 3
0.7379	Intermediate Similarity	NPD5126	Approved
0.7349	Intermediate Similarity	NPD7058	Phase 2
0.7349	Intermediate Similarity	NPD7057	Phase 3
0.733	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8407	Phase 2
0.7267	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD8166	Discontinued
0.72	Intermediate Similarity	NPD8368	Discontinued
0.7168	Intermediate Similarity	NPD7228	Approved
0.7152	Intermediate Similarity	NPD7028	Phase 2
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4965	Approved
0.7143	Intermediate Similarity	NPD4967	Phase 2
0.7143	Intermediate Similarity	NPD7961	Discontinued
0.7095	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD37	Approved
0.7063	Intermediate Similarity	NPD6858	Approved
0.7063	Intermediate Similarity	NPD7094	Approved
0.7034	Intermediate Similarity	NPD4198	Discontinued
0.7032	Intermediate Similarity	NPD6663	Approved
0.7024	Intermediate Similarity	NPD8455	Phase 2
0.7017	Intermediate Similarity	NPD8361	Approved
0.7017	Intermediate Similarity	NPD8360	Approved
0.7017	Intermediate Similarity	NPD8435	Approved
0.7012	Intermediate Similarity	NPD6273	Approved
0.7006	Intermediate Similarity	NPD7240	Approved
0.7006	Intermediate Similarity	NPD7685	Pre-registration
0.7	Intermediate Similarity	NPD7507	Approved
0.6988	Remote Similarity	NPD7458	Discontinued
0.6977	Remote Similarity	NPD7199	Phase 2
0.6966	Remote Similarity	NPD2629	Approved
0.6959	Remote Similarity	NPD8033	Approved
0.6959	Remote Similarity	NPD6234	Discontinued
0.6951	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8312	Approved
0.6927	Remote Similarity	NPD8313	Approved
0.6923	Remote Similarity	NPD5761	Phase 2
0.6923	Remote Similarity	NPD5760	Phase 2
0.6914	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6764	Approved
0.691	Remote Similarity	NPD6765	Approved
0.6906	Remote Similarity	NPD8434	Phase 2
0.6903	Remote Similarity	NPD7008	Discontinued
0.6892	Remote Similarity	NPD8377	Approved
0.6892	Remote Similarity	NPD8294	Approved
0.689	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5736	Approved
0.6863	Remote Similarity	NPD7319	Approved
0.6862	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7097	Phase 1
0.6848	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD8378	Approved
0.6846	Remote Similarity	NPD8335	Approved
0.6846	Remote Similarity	NPD8380	Approved
0.6846	Remote Similarity	NPD7503	Approved
0.6846	Remote Similarity	NPD8379	Approved
0.6846	Remote Similarity	NPD8296	Approved
0.6832	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6004	Phase 3
0.6832	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6005	Phase 3
0.6832	Remote Similarity	NPD7266	Discontinued
0.6832	Remote Similarity	NPD6002	Phase 3
0.6813	Remote Similarity	NPD8150	Discontinued
0.681	Remote Similarity	NPD4628	Phase 3
0.68	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7736	Approved
0.6768	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6785	Approved
0.6758	Remote Similarity	NPD6784	Approved
0.6757	Remote Similarity	NPD7327	Approved
0.6757	Remote Similarity	NPD7328	Approved
0.6754	Remote Similarity	NPD7497	Discontinued
0.6752	Remote Similarity	NPD3764	Approved
0.6728	Remote Similarity	NPD5762	Approved
0.6728	Remote Similarity	NPD5763	Approved
0.6728	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7516	Approved
0.6711	Remote Similarity	NPD7610	Discontinued
0.6709	Remote Similarity	NPD8032	Phase 2
0.6702	Remote Similarity	NPD8485	Approved
0.669	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7115	Discovery
0.6689	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD4140	Approved
0.6649	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5844	Phase 1
0.6644	Remote Similarity	NPD969	Suspended
0.6643	Remote Similarity	NPD6685	Approved
0.6625	Remote Similarity	NPD6355	Discontinued
0.6624	Remote Similarity	NPD7055	Discontinued
0.6623	Remote Similarity	NPD7078	Approved
0.6622	Remote Similarity	NPD5951	Approved
0.6606	Remote Similarity	NPD7003	Approved
0.6605	Remote Similarity	NPD7305	Phase 1
0.6604	Remote Similarity	NPD7715	Approved
0.6604	Remote Similarity	NPD7714	Approved
0.6601	Remote Similarity	NPD7492	Approved
0.6597	Remote Similarity	NPD6686	Approved
0.6588	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7680	Approved
0.6579	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6190	Approved
0.6558	Remote Similarity	NPD6616	Approved
0.6556	Remote Similarity	NPD6054	Approved
0.6554	Remote Similarity	NPD6010	Discontinued
0.6554	Remote Similarity	NPD3787	Discontinued
0.6552	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD8320	Phase 1
0.6546	Remote Similarity	NPD8319	Approved
0.6545	Remote Similarity	NPD6674	Discontinued
0.6538	Remote Similarity	NPD6559	Discontinued
0.6532	Remote Similarity	NPD7819	Suspended
0.6522	Remote Similarity	NPD5735	Approved
0.651	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2067	Discontinued
0.6506	Remote Similarity	NPD4110	Phase 3
0.6506	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6085	Phase 2
0.6492	Remote Similarity	NPD7699	Phase 2
0.6492	Remote Similarity	NPD7700	Phase 2
0.6486	Remote Similarity	NPD8133	Approved
0.6482	Remote Similarity	NPD8462	Phase 1
0.6471	Remote Similarity	NPD6370	Approved
0.6471	Remote Similarity	NPD3019	Approved
0.6471	Remote Similarity	NPD2932	Approved
0.6464	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD2182	Approved
0.6437	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6647	Phase 2
0.6434	Remote Similarity	NPD5765	Approved
0.6433	Remote Similarity	NPD3094	Phase 2
0.6421	Remote Similarity	NPD6535	Approved
0.6421	Remote Similarity	NPD6534	Approved
0.642	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.641	Remote Similarity	NPD8293	Discontinued
0.641	Remote Similarity	NPD7435	Discontinued
0.6405	Remote Similarity	NPD8516	Approved
0.6405	Remote Similarity	NPD6016	Approved
0.6405	Remote Similarity	NPD8515	Approved
0.6405	Remote Similarity	NPD6015	Approved
0.6405	Remote Similarity	NPD8513	Phase 3
0.6405	Remote Similarity	NPD8517	Approved
0.6402	Remote Similarity	NPD7033	Discontinued
0.6383	Remote Similarity	NPD7638	Approved
0.638	Remote Similarity	NPD6653	Approved
0.638	Remote Similarity	NPD6353	Approved
0.6375	Remote Similarity	NPD7095	Approved
0.6374	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6099	Approved
0.6364	Remote Similarity	NPD5988	Approved
0.6364	Remote Similarity	NPD7768	Phase 2
0.6364	Remote Similarity	NPD7137	Phase 2
0.6364	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6100	Approved
0.6358	Remote Similarity	NPD4380	Phase 2
0.6358	Remote Similarity	NPD6009	Approved
0.6352	Remote Similarity	NPD7084	Phase 3
0.6351	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7999	Approved
0.634	Remote Similarity	NPD7009	Phase 2
0.634	Remote Similarity	NPD6059	Approved
0.6339	Remote Similarity	NPD7074	Phase 3
0.6338	Remote Similarity	NPD7798	Approved
0.6338	Remote Similarity	NPD7639	Approved
0.6338	Remote Similarity	NPD7640	Approved
0.6335	Remote Similarity	NPD6798	Discontinued
0.6333	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7075	Discontinued
0.6327	Remote Similarity	NPD7696	Phase 3
0.6327	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7697	Approved
0.6327	Remote Similarity	NPD7698	Approved
0.6325	Remote Similarity	NPD2346	Discontinued
0.6324	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD3026	Approved
0.6323	Remote Similarity	NPD3023	Approved
0.6322	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD5124	Phase 1
0.6319	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3750	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