NPASS Compound

Structure

CID321072 OpenBabel06191716152D 59 65 0 0 1 0 0 0 0 0999 V2000 -3.1053 0.5563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8319 3.1046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4884 3.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5685 3.2610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2520 0.8572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2529 -0.2081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9330 -5.5177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2310 3.0651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5168 0.3568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1318 -1.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1969 -4.9529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7902 -5.1626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6662 3.8012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8759 2.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6596 0.0017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2746 -1.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3180 -4.0330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9113 -4.2427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7463 3.6801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9560 2.0868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8035 -1.3918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0985 1.4040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9278 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4616 1.2246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0720 2.2084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5385 -0.9182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1752 -3.6779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3912 2.8229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7369 0.9861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6071 -0.9278 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9278 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7271 1.9399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6813 -1.2733 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.9672 1.0437 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9452 -0.7084 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8035 0.4639 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5033 0.2401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5634 1.3601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2963 -2.7580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4713 2.7018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0880 -1.0635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9235 2.4038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6071 0.0000 0.0000 C 0 0 1 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 -1.0273 2.1637 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5602 -2.1932 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9682 1.9682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4106 -1.3918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8871 0.9226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0663 0.2115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0681 -0.4960 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1535 -2.4029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9065 3.4379 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9669 -1.9834 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6973 3.0308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9278 -0.9278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6158 0.0662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1162 1.8446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2401 0.8962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 42 1 0 0 0 0 4 42 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 15 26 2 0 0 0 0 16 26 1 0 0 0 0 17 27 2 0 0 0 0 18 27 1 0 0 0 0 19 28 2 0 0 0 0 20 28 1 0 0 0 0 21 30 1 0 0 0 0 21 31 1 0 0 0 0 22 29 1 0 0 0 0 22 45 1 0 0 0 0 23 44 1 0 0 0 0 23 56 1 0 0 0 0 24 29 1 0 0 0 0 24 32 2 0 0 0 0 25 47 2 0 0 0 0 25 59 1 0 0 0 0 26 33 1 0 0 0 0 27 39 1 0 0 0 0 28 40 1 0 0 0 0 29 57 1 6 0 0 0 30 43 1 1 0 0 0 30 48 1 0 0 0 0 31 44 1 6 0 0 0 31 56 1 0 0 0 0 32 34 1 0 0 0 0 32 42 1 0 0 0 0 33 35 1 0 0 0 0 33 46 1 0 0 0 0 34 37 1 0 0 0 0 34 49 1 6 0 0 0 35 41 1 0 0 0 0 35 50 1 1 0 0 0 36 38 1 0 0 0 0 36 43 1 6 0 0 0 36 44 1 0 0 0 0 37 43 1 0 0 0 0 37 51 2 0 0 0 0 38 45 1 1 0 0 0 38 58 1 0 0 0 0 39 46 2 3 0 0 0 39 52 1 0 0 0 0 40 53 2 0 0 0 0 40 58 1 0 0 0 0 41 54 2 0 0 0 0 41 57 1 0 0 0 0 42 45 1 0 0 0 0 43 5 1 6 0 0 0 44 59 1 1 0 0 0 45 55 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	811.32
Volume:	812.703
LogP:	3.523
LogD:	2.092
LogS:	-4.604
# Rotatable Bonds:	13
TPSA:	212.06
# H-Bond Aceptor:	14
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.139
Synthetic Accessibility Score:	6.002
Fsp3:	0.467
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.521
MDCK Permeability:	4.2599222069839016e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.26
20% Bioavailability (F20%):	0.672
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	93.10153198242188%
Volume Distribution (VD):	0.967
Pgp-substrate:	6.200120449066162%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.527
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.754
CYP3A4-substrate:	0.676

ADMET: Excretion

Clearance (CL):	4.225
Half-life (T1/2):	0.021

ADMET: Toxicity

hERG Blockers:	0.465
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.346
Maximum Recommended Daily Dose:	0.71
Skin Sensitization:	0.028
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.353

Download Data

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

Natural Product: NPC321072

Natural Product ID:	NPC321072
*Common Name:**	TYLVGQKNNUHXIP-SEWFTMAUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TYLVGQKNNUHXIP-SEWFTMAUSA-N
Standard InCHI:	InChI=1S/C45H49NO13/c1-24-29(57-41(54)35(50)33(26-15-9-6-10-16-26)46-39(52)27-17-11-7-12-18-27)22-45(55)38(58-40(53)28-19-13-8-14-20-28)36-43(5,37(51)34(49)32(24)42(45,3)4)30(48)21-31-44(36,23-56-31)59-25(2)47/h6-20,29-31,33-36,38,48-50,55H,21-23H2,1-5H3,(H,46,52)/t29-,30+,31+,33?,34+,35+,36-,38-,43+,44-,45+/m0/s1
SMILES:	CC(=O)O[C@@]12CO[C@@H]1C[C@H]([C@@]1([C@@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)C[C@H](OC(=O)[C@@H](C(c3ccccc3)N=C(c3ccccc3)O)O)C(=C(C2(C)C)[C@H](C1=O)O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2111849
PubChem CID:	71449052
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes 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
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23265441]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28240909]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28581744]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264680]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561894]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7908950]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23720	Taxus wallichiana	Species	Taxaceae	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	2
Others	2

Activity Type	# Activity
Cell Line	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.71	ug.mL-1	PMID[567517]
NPT2	Others	Unspecified		Control	=	192.0	%	PMID[567517]
NPT2	Others	Unspecified		Control	=	218.0	%	PMID[567517]
NPT27	Others	Unspecified		IC50	=	0.013	ug.mL-1	PMID[567517]

☑ 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 NPC321072 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	262
0.1-0.2	1078
0.2-0.3	2643
0.3-0.4	7368
0.4-0.5	13277
0.5-0.6	13376
0.6-0.7	4377
0.7-0.8	256
0.8-0.85	12
0.85-0.9	1
0.9-0.95	24
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC215892
1.0	High Similarity	NPC242662
1.0	High Similarity	NPC191193
0.9943	High Similarity	NPC181964
0.9943	High Similarity	NPC471606
0.9943	High Similarity	NPC208553
0.9886	High Similarity	NPC473558
0.9773	High Similarity	NPC473490
0.9769	High Similarity	NPC475336
0.9769	High Similarity	NPC453583
0.9769	High Similarity	NPC473300
0.9713	High Similarity	NPC67246
0.9713	High Similarity	NPC33372
0.9655	High Similarity	NPC471754
0.9655	High Similarity	NPC317882
0.9653	High Similarity	NPC327699
0.9611	High Similarity	NPC289383
0.9558	High Similarity	NPC116862
0.9543	High Similarity	NPC306001
0.9543	High Similarity	NPC206211
0.9543	High Similarity	NPC324251
0.9543	High Similarity	NPC275170
0.9543	High Similarity	NPC471629
0.9543	High Similarity	NPC473400
0.9444	High Similarity	NPC472392
0.9392	High Similarity	NPC472391
0.9375	High Similarity	NPC471623
0.9337	High Similarity	NPC472375
0.8859	High Similarity	NPC36607
0.8266	Intermediate Similarity	NPC134685
0.8266	Intermediate Similarity	NPC11588
0.8266	Intermediate Similarity	NPC229545
0.8266	Intermediate Similarity	NPC248265
0.8218	Intermediate Similarity	NPC259144
0.8218	Intermediate Similarity	NPC228204
0.8218	Intermediate Similarity	NPC26033
0.8218	Intermediate Similarity	NPC114357
0.8218	Intermediate Similarity	NPC155329
0.8161	Intermediate Similarity	NPC219419
0.8161	Intermediate Similarity	NPC472005
0.8161	Intermediate Similarity	NPC265395
0.8161	Intermediate Similarity	NPC237549
0.8161	Intermediate Similarity	NPC158333
0.8161	Intermediate Similarity	NPC473414
0.8161	Intermediate Similarity	NPC242262
0.8161	Intermediate Similarity	NPC472030
0.8161	Intermediate Similarity	NPC304876
0.8161	Intermediate Similarity	NPC249471
0.8161	Intermediate Similarity	NPC256142
0.8161	Intermediate Similarity	NPC257213
0.8161	Intermediate Similarity	NPC1173
0.8161	Intermediate Similarity	NPC472022
0.815	Intermediate Similarity	NPC197037
0.8125	Intermediate Similarity	NPC472393
0.8114	Intermediate Similarity	NPC112523
0.8114	Intermediate Similarity	NPC114410
0.8092	Intermediate Similarity	NPC91730
0.8092	Intermediate Similarity	NPC7095
0.8079	Intermediate Similarity	NPC471102
0.8068	Intermediate Similarity	NPC217091
0.8068	Intermediate Similarity	NPC106895
0.8057	Intermediate Similarity	NPC77719
0.8056	Intermediate Similarity	NPC471493
0.8035	Intermediate Similarity	NPC250046
0.8035	Intermediate Similarity	NPC60509
0.8035	Intermediate Similarity	NPC81698
0.8023	Intermediate Similarity	NPC469771
0.8011	Intermediate Similarity	NPC472549
0.8011	Intermediate Similarity	NPC21410
0.8011	Intermediate Similarity	NPC473670
0.8011	Intermediate Similarity	NPC282239
0.7989	Intermediate Similarity	NPC161239
0.7989	Intermediate Similarity	NPC165260
0.7989	Intermediate Similarity	NPC112216
0.7989	Intermediate Similarity	NPC198455
0.7989	Intermediate Similarity	NPC476077
0.7977	Intermediate Similarity	NPC217918
0.7943	Intermediate Similarity	NPC470153
0.7898	Intermediate Similarity	NPC477905
0.7898	Intermediate Similarity	NPC472548
0.7861	Intermediate Similarity	NPC127857
0.7841	Intermediate Similarity	NPC101043
0.7841	Intermediate Similarity	NPC471103
0.7841	Intermediate Similarity	NPC306799
0.7841	Intermediate Similarity	NPC51602
0.7809	Intermediate Similarity	NPC469730
0.7809	Intermediate Similarity	NPC132599
0.7809	Intermediate Similarity	NPC473632
0.7809	Intermediate Similarity	NPC473611
0.7803	Intermediate Similarity	NPC38696
0.7784	Intermediate Similarity	NPC470245
0.7784	Intermediate Similarity	NPC254558
0.7784	Intermediate Similarity	NPC473214
0.7727	Intermediate Similarity	NPC270590
0.7727	Intermediate Similarity	NPC301556
0.7727	Intermediate Similarity	NPC473215
0.7727	Intermediate Similarity	NPC476975
0.7727	Intermediate Similarity	NPC92293
0.7727	Intermediate Similarity	NPC471101
0.7727	Intermediate Similarity	NPC266265
0.7714	Intermediate Similarity	NPC474935
0.7688	Intermediate Similarity	NPC34012
0.767	Intermediate Similarity	NPC281717
0.7657	Intermediate Similarity	NPC174982
0.7657	Intermediate Similarity	NPC473088
0.7657	Intermediate Similarity	NPC472575
0.7657	Intermediate Similarity	NPC184817
0.7657	Intermediate Similarity	NPC470157
0.7657	Intermediate Similarity	NPC29704
0.7657	Intermediate Similarity	NPC158663
0.7657	Intermediate Similarity	NPC472572
0.7657	Intermediate Similarity	NPC472568
0.7657	Intermediate Similarity	NPC171525
0.7657	Intermediate Similarity	NPC472571
0.7657	Intermediate Similarity	NPC471104
0.7657	Intermediate Similarity	NPC177940
0.7657	Intermediate Similarity	NPC200471
0.7657	Intermediate Similarity	NPC476973
0.7657	Intermediate Similarity	NPC70403
0.7657	Intermediate Similarity	NPC470159
0.7657	Intermediate Similarity	NPC472556
0.7657	Intermediate Similarity	NPC96903
0.7657	Intermediate Similarity	NPC469349
0.7622	Intermediate Similarity	NPC30171
0.76	Intermediate Similarity	NPC472573
0.76	Intermediate Similarity	NPC472570
0.76	Intermediate Similarity	NPC188865
0.76	Intermediate Similarity	NPC25768
0.76	Intermediate Similarity	NPC95810
0.76	Intermediate Similarity	NPC70716
0.76	Intermediate Similarity	NPC11685
0.76	Intermediate Similarity	NPC163719
0.76	Intermediate Similarity	NPC125106
0.76	Intermediate Similarity	NPC241951
0.76	Intermediate Similarity	NPC475759
0.76	Intermediate Similarity	NPC475122
0.76	Intermediate Similarity	NPC57628
0.76	Intermediate Similarity	NPC470152
0.76	Intermediate Similarity	NPC472569
0.76	Intermediate Similarity	NPC476974
0.76	Intermediate Similarity	NPC95265
0.7586	Intermediate Similarity	NPC182869
0.7582	Intermediate Similarity	NPC469399
0.7569	Intermediate Similarity	NPC11410
0.7568	Intermediate Similarity	NPC471134
0.7557	Intermediate Similarity	NPC471107
0.7557	Intermediate Similarity	NPC471100
0.7557	Intermediate Similarity	NPC277053
0.7557	Intermediate Similarity	NPC301946
0.7543	Intermediate Similarity	NPC477894
0.7543	Intermediate Similarity	NPC163087
0.754	Intermediate Similarity	NPC102465
0.7529	Intermediate Similarity	NPC213567
0.7527	Intermediate Similarity	NPC469417
0.7514	Intermediate Similarity	NPC329960
0.7514	Intermediate Similarity	NPC295408
0.7514	Intermediate Similarity	NPC472371
0.7514	Intermediate Similarity	NPC66193
0.7514	Intermediate Similarity	NPC472395
0.7514	Intermediate Similarity	NPC94602
0.7514	Intermediate Similarity	NPC150893
0.7514	Intermediate Similarity	NPC251139
0.75	Intermediate Similarity	NPC471912
0.75	Intermediate Similarity	NPC477473
0.75	Intermediate Similarity	NPC80895
0.75	Intermediate Similarity	NPC278272
0.75	Intermediate Similarity	NPC477466
0.75	Intermediate Similarity	NPC477469
0.75	Intermediate Similarity	NPC470231
0.75	Intermediate Similarity	NPC120667
0.75	Intermediate Similarity	NPC477471
0.7486	Intermediate Similarity	NPC31829
0.7474	Intermediate Similarity	NPC469421
0.7459	Intermediate Similarity	NPC253738
0.7458	Intermediate Similarity	NPC473541
0.7454	Intermediate Similarity	NPC150698
0.7454	Intermediate Similarity	NPC96801
0.745	Intermediate Similarity	NPC42286
0.7448	Intermediate Similarity	NPC475649
0.7447	Intermediate Similarity	NPC469420
0.7443	Intermediate Similarity	NPC246480
0.7443	Intermediate Similarity	NPC139067
0.7443	Intermediate Similarity	NPC473673
0.7443	Intermediate Similarity	NPC270498
0.7443	Intermediate Similarity	NPC147217
0.7443	Intermediate Similarity	NPC177340
0.7443	Intermediate Similarity	NPC191082
0.7443	Intermediate Similarity	NPC477468
0.7443	Intermediate Similarity	NPC475429
0.7438	Intermediate Similarity	NPC314941
0.7433	Intermediate Similarity	NPC61891
0.7429	Intermediate Similarity	NPC87448
0.7429	Intermediate Similarity	NPC16912
0.7429	Intermediate Similarity	NPC41481
0.7429	Intermediate Similarity	NPC472576
0.7429	Intermediate Similarity	NPC27377
0.7429	Intermediate Similarity	NPC224491
0.7429	Intermediate Similarity	NPC97947
0.7429	Intermediate Similarity	NPC291599
0.7429	Intermediate Similarity	NPC118080

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 NPC321072 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	556
0.2-0.3	1024
0.3-0.4	2311
0.4-0.5	3380
0.5-0.6	1459
0.6-0.7	213
0.7-0.8	15
0.8-0.85	3
0.85-0.9	3
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9943	High Similarity	NPD8485	Approved
0.9774	High Similarity	NPD8486	Clinical (unspecified phase)
0.9486	High Similarity	NPD8360	Approved
0.9486	High Similarity	NPD8361	Approved
0.9375	High Similarity	NPD8435	Approved
0.9045	High Similarity	NPD8424	Clinical (unspecified phase)
0.8764	High Similarity	NPD8368	Discontinued
0.8722	High Similarity	NPD8407	Phase 2
0.8492	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD8462	Phase 1
0.8159	Intermediate Similarity	NPD8404	Phase 2
0.7656	Intermediate Similarity	NPD8150	Discontinued
0.7512	Intermediate Similarity	NPD7874	Approved
0.7512	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7801	Approved
0.7474	Intermediate Similarity	NPD8434	Phase 2
0.7438	Intermediate Similarity	NPD8319	Approved
0.7438	Intermediate Similarity	NPD8320	Phase 1
0.7406	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7699	Phase 2
0.74	Intermediate Similarity	NPD7700	Phase 2
0.7337	Intermediate Similarity	NPD6534	Approved
0.7337	Intermediate Similarity	NPD6535	Approved
0.7295	Intermediate Similarity	NPD8151	Discontinued
0.7184	Intermediate Similarity	NPD7871	Phase 2
0.7184	Intermediate Similarity	NPD7870	Phase 2
0.7171	Intermediate Similarity	NPD6823	Phase 2
0.7163	Intermediate Similarity	NPD7701	Phase 2
0.7157	Intermediate Similarity	NPD6780	Approved
0.7157	Intermediate Similarity	NPD6778	Approved
0.7157	Intermediate Similarity	NPD6781	Approved
0.7157	Intermediate Similarity	NPD6782	Approved
0.7157	Intermediate Similarity	NPD6779	Approved
0.7157	Intermediate Similarity	NPD6777	Approved
0.7157	Intermediate Similarity	NPD6776	Approved
0.7136	Intermediate Similarity	NPD7696	Phase 3
0.7136	Intermediate Similarity	NPD7698	Approved
0.7136	Intermediate Similarity	NPD7697	Approved
0.7128	Intermediate Similarity	NPD5030	Phase 2
0.7111	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7799	Discontinued
0.7092	Intermediate Similarity	NPD5026	Approved
0.7092	Intermediate Similarity	NPD4954	Approved
0.7092	Intermediate Similarity	NPD4955	Approved
0.7092	Intermediate Similarity	NPD5034	Approved
0.7092	Intermediate Similarity	NPD36	Approved
0.7092	Intermediate Similarity	NPD5028	Approved
0.7071	Intermediate Similarity	NPD5036	Approved
0.7053	Intermediate Similarity	NPD7435	Discontinued
0.7035	Intermediate Similarity	NPD5038	Approved
0.7035	Intermediate Similarity	NPD5037	Approved
0.699	Remote Similarity	NPD3823	Discontinued
0.6987	Remote Similarity	NPD8468	Phase 2
0.6978	Remote Similarity	NPD7236	Approved
0.6973	Remote Similarity	NPD7239	Suspended
0.6905	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7497	Discontinued
0.6847	Remote Similarity	NPD8059	Phase 3
0.6847	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7783	Phase 2
0.6822	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5035	Approved
0.6796	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5031	Approved
0.6784	Remote Similarity	NPD5029	Approved
0.6784	Remote Similarity	NPD5027	Approved
0.6763	Remote Similarity	NPD7282	Approved
0.6732	Remote Similarity	NPD5968	Phase 3
0.6716	Remote Similarity	NPD6836	Approved
0.6699	Remote Similarity	NPD6212	Phase 3
0.6699	Remote Similarity	NPD6213	Phase 3
0.6699	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.665	Remote Similarity	NPD3819	Phase 2
0.6634	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7907	Approved
0.6619	Remote Similarity	NPD7811	Phase 3
0.6619	Remote Similarity	NPD7810	Phase 3
0.6615	Remote Similarity	NPD7972	Discontinued
0.6588	Remote Similarity	NPD4914	Approved
0.6579	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.657	Remote Similarity	NPD8146	Phase 2
0.6566	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8312	Approved
0.6552	Remote Similarity	NPD8313	Approved
0.6546	Remote Similarity	NPD7058	Phase 2
0.6546	Remote Similarity	NPD7057	Phase 3
0.654	Remote Similarity	NPD7565	Approved
0.654	Remote Similarity	NPD8285	Discontinued
0.6535	Remote Similarity	NPD8067	Phase 3
0.6532	Remote Similarity	NPD4665	Approved
0.6531	Remote Similarity	NPD6746	Phase 2
0.6505	Remote Similarity	NPD2575	Approved
0.6502	Remote Similarity	NPD5032	Approved
0.6485	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD8366	Approved
0.6471	Remote Similarity	NPD6190	Approved
0.6462	Remote Similarity	NPD5544	Approved
0.6457	Remote Similarity	NPD4111	Phase 1
0.645	Remote Similarity	NPD7473	Discontinued
0.6449	Remote Similarity	NPD4387	Approved
0.6449	Remote Similarity	NPD4386	Approved
0.6436	Remote Similarity	NPD3300	Phase 2
0.6432	Remote Similarity	NPD8491	Approved
0.6432	Remote Similarity	NPD5242	Approved
0.6429	Remote Similarity	NPD7075	Discontinued
0.6418	Remote Similarity	NPD7177	Discontinued
0.6417	Remote Similarity	NPD8166	Discontinued
0.6416	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD7713	Phase 3
0.6409	Remote Similarity	NPD7714	Approved
0.6409	Remote Similarity	NPD7715	Approved
0.64	Remote Similarity	NPD6166	Phase 2
0.64	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5844	Phase 1
0.6381	Remote Similarity	NPD4466	Phase 1
0.6376	Remote Similarity	NPD7654	Discontinued
0.6374	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7460	Discontinued
0.6355	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7930	Approved
0.634	Remote Similarity	NPD6385	Approved
0.634	Remote Similarity	NPD6386	Approved
0.6337	Remote Similarity	NPD3751	Discontinued
0.633	Remote Similarity	NPD3400	Discontinued
0.633	Remote Similarity	NPD4628	Phase 3
0.633	Remote Similarity	NPD7584	Approved
0.633	Remote Similarity	NPD7583	Approved
0.6327	Remote Similarity	NPD5402	Approved
0.6326	Remote Similarity	NPD2493	Approved
0.6326	Remote Similarity	NPD3452	Approved
0.6326	Remote Similarity	NPD2494	Approved
0.6326	Remote Similarity	NPD3450	Approved
0.6321	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7458	Discontinued
0.6318	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD4583	Approved
0.6313	Remote Similarity	NPD4582	Approved
0.6311	Remote Similarity	NPD7546	Discontinued
0.6308	Remote Similarity	NPD6801	Discontinued
0.6308	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7029	Discontinued
0.6307	Remote Similarity	NPD6287	Discontinued
0.6305	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7585	Approved
0.63	Remote Similarity	NPD7315	Approved
0.63	Remote Similarity	NPD6232	Discontinued
0.6298	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD7008	Discontinued
0.6294	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7038	Approved
0.6293	Remote Similarity	NPD7039	Approved
0.6291	Remote Similarity	NPD2973	Approved
0.6291	Remote Similarity	NPD2974	Approved
0.6291	Remote Similarity	NPD2975	Approved
0.6289	Remote Similarity	NPD6502	Phase 2
0.6289	Remote Similarity	NPD4380	Phase 2
0.6289	Remote Similarity	NPD6599	Discontinued
0.6286	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD7999	Approved
0.6279	Remote Similarity	NPD4580	Approved
0.6276	Remote Similarity	NPD7819	Suspended
0.6268	Remote Similarity	NPD7693	Approved
0.6267	Remote Similarity	NPD4004	Approved
0.6267	Remote Similarity	NPD4002	Approved
0.6263	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4974	Approved
0.6262	Remote Similarity	NPD7962	Phase 2
0.6262	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4975	Approved
0.6256	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6255	Remote Similarity	NPD7048	Phase 3
0.625	Remote Similarity	NPD8127	Discontinued
0.6244	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6894	Phase 1
0.6237	Remote Similarity	NPD3455	Phase 2
0.6233	Remote Similarity	NPD5608	Approved
0.6233	Remote Similarity	NPD6874	Approved
0.6233	Remote Similarity	NPD5609	Approved
0.623	Remote Similarity	NPD7961	Discontinued
0.6228	Remote Similarity	NPD6997	Phase 2
0.6224	Remote Similarity	NPD7011	Discontinued
0.6221	Remote Similarity	NPD3057	Approved
0.622	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD3787	Discontinued
0.6216	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5039	Approved
0.6209	Remote Similarity	NPD4738	Phase 2
0.6198	Remote Similarity	NPD8367	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