NPASS Compound

Structure

NPC473558 OpenBabel07101719142D 65 71 0 0 1 0 0 0 0 0999 V2000 -3.2099 -0.5751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6612 2.8772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8501 -0.0018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1081 -2.2827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5721 -3.2456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6213 -3.3708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2941 -0.8861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4633 4.1687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1440 0.4319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5390 -2.9179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7024 3.5849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3494 3.8017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3831 -0.1520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0188 1.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1720 -2.0318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9551 -3.6788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8276 2.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4745 2.8508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4970 0.2151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1327 1.7498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2211 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0043 -3.5536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8306 1.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1355 -1.4513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9591 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5445 -1.2658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4917 2.3977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0892 -0.5856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1817 -2.5309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7137 2.2670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3719 1.1659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6373 -2.6675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7953 -1.0193 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6612 0.9591 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9591 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8188 -2.0052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8389 1.3161 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0671 -1.0788 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0780 0.7323 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8306 -0.4795 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5875 -0.2482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5824 -1.4059 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4858 1.5329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6864 -2.5423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1919 1.0993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9883 -2.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6612 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 -1.0619 -2.2365 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7249 0.9491 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3223 2.8772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2144 -1.5365 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0665 -3.4573 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0179 -0.9536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1714 0.5127 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3606 2.4838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1025 -3.3032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0667 2.0501 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7207 -3.1328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9591 0.9591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4917 1.4386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2032 -0.2186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6702 -0.0684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3194 -1.6563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4964 -1.8528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 46 1 0 0 0 0 6 46 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 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 21 1 0 0 0 0 16 22 2 0 0 0 0 17 30 2 0 0 0 0 18 30 1 0 0 0 0 19 31 2 0 0 0 0 20 31 1 0 0 0 0 21 32 2 0 0 0 0 22 32 1 0 0 0 0 23 34 1 0 0 0 0 23 35 1 0 0 0 0 24 33 1 0 0 0 0 24 49 1 0 0 0 0 25 48 1 0 0 0 0 25 60 1 0 0 0 0 26 33 1 0 0 0 0 26 36 2 0 0 0 0 27 51 2 0 0 0 0 27 61 1 0 0 0 0 28 52 2 0 0 0 0 28 62 1 0 0 0 0 29 53 2 0 0 0 0 29 65 1 0 0 0 0 30 37 1 0 0 0 0 31 43 1 0 0 0 0 32 44 1 0 0 0 0 33 63 1 1 0 0 0 34 47 1 1 0 0 0 34 61 1 0 0 0 0 35 48 1 1 0 0 0 35 60 1 0 0 0 0 36 38 1 0 0 0 0 36 46 1 0 0 0 0 37 39 1 0 0 0 0 37 50 1 1 0 0 0 38 41 1 0 0 0 0 38 54 1 1 0 0 0 39 45 1 6 0 0 0 39 62 1 0 0 0 0 40 42 1 0 0 0 0 40 47 1 1 0 0 0 40 48 1 0 0 0 0 41 47 1 0 0 0 0 41 55 2 0 0 0 0 42 49 1 6 0 0 0 42 64 1 0 0 0 0 43 50 2 3 0 0 0 43 56 1 0 0 0 0 44 57 2 0 0 0 0 44 64 1 0 0 0 0 45 58 2 0 0 0 0 45 63 1 0 0 0 0 46 49 1 0 0 0 0 47 7 1 1 0 0 0 48 65 1 6 0 0 0 49 59 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	895.34
Volume:	894.195
LogP:	4.091
LogD:	2.207
LogS:	-4.446
# Rotatable Bonds:	17
TPSA:	224.2
# H-Bond Aceptor:	16
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.154
Synthetic Accessibility Score:	6.225
Fsp3:	0.469
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:	-5.332
MDCK Permeability:	7.414940046146512e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.769
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	83.55339813232422%
Volume Distribution (VD):	1.449
Pgp-substrate:	7.0227437019348145%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.595
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.684
CYP3A4-substrate:	0.728

ADMET: Excretion

Clearance (CL):	3.194
Half-life (T1/2):	0.012

ADMET: Toxicity

hERG Blockers:	0.274
Human Hepatotoxicity (H-HT):	0.981
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.633
Maximum Recommended Daily Dose:	0.641
Skin Sensitization:	0.04
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.172

Download Data

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

Natural Product: NPC473558

Natural Product ID:	NPC473558
*Common Name:**	TYGGBZFXLTZBPR-XOVTVWCYSA-N
IUPAC Name:	n.a.
Synonyms:	10-Deacetyltaxol 2',7-Diacetate
Standard InCHIKey:	TYGGBZFXLTZBPR-XOVTVWCYSA-N
Standard InCHI:	InChI=1S/C49H53NO15/c1-26-33(63-45(58)39(62-28(3)52)37(30-17-11-8-12-18-30)50-43(56)31-19-13-9-14-20-31)24-49(59)42(64-44(57)32-21-15-10-16-22-32)40-47(7,41(55)38(54)36(26)46(49,5)6)34(61-27(2)51)23-35-48(40,25-60-35)65-29(4)53/h8-22,33-35,37-40,42,54,59H,23-25H2,1-7H3,(H,50,56)/t33-,34-,35+,37-,38+,39+,40-,42-,47+,48-,49+/m0/s1
SMILES:	CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)OC(=O)C)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)OC(=O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445692
PubChem CID:	44593345
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
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955887]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2878063]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7130988]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	bark	n.a.	n.a.	PMID[7623034]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27064	Taxus brevifolia	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
ED50	2
Others	1

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	<	1.0	10'-2 ug/ml	PMID[542215]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	16.0	%	PMID[542216]
NPT2	Others	Unspecified		ED50	<	0.01	ug ml-1	PMID[542216]

☑ 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 NPC473558 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	264
0.1-0.2	1111
0.2-0.3	2697
0.3-0.4	7652
0.4-0.5	13496
0.5-0.6	13286
0.6-0.7	3916
0.7-0.8	215
0.8-0.85	12
0.85-0.9	1
0.9-0.95	26
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9943	High Similarity	NPC181964
0.9943	High Similarity	NPC471606
0.9943	High Similarity	NPC208553
0.9886	High Similarity	NPC321072
0.9886	High Similarity	NPC473490
0.9886	High Similarity	NPC191193
0.9886	High Similarity	NPC215892
0.9886	High Similarity	NPC242662
0.9714	High Similarity	NPC33372
0.9714	High Similarity	NPC67246
0.9657	High Similarity	NPC473300
0.9657	High Similarity	NPC475336
0.9657	High Similarity	NPC453583
0.956	High Similarity	NPC116862
0.9545	High Similarity	NPC306001
0.9545	High Similarity	NPC471754
0.9545	High Similarity	NPC206211
0.9545	High Similarity	NPC324251
0.9545	High Similarity	NPC275170
0.9545	High Similarity	NPC471629
0.9545	High Similarity	NPC473400
0.9545	High Similarity	NPC317882
0.9543	High Similarity	NPC327699
0.9505	High Similarity	NPC289383
0.9396	High Similarity	NPC472391
0.9379	High Similarity	NPC471623
0.9341	High Similarity	NPC472392
0.9235	High Similarity	NPC472375
0.8865	High Similarity	NPC36607
0.8229	Intermediate Similarity	NPC114357
0.8229	Intermediate Similarity	NPC155329
0.8229	Intermediate Similarity	NPC259144
0.8171	Intermediate Similarity	NPC11588
0.8171	Intermediate Similarity	NPC229545
0.8171	Intermediate Similarity	NPC248265
0.8171	Intermediate Similarity	NPC219419
0.8171	Intermediate Similarity	NPC134685
0.8136	Intermediate Similarity	NPC472393
0.8125	Intermediate Similarity	NPC228204
0.8125	Intermediate Similarity	NPC26033
0.809	Intermediate Similarity	NPC471102
0.8079	Intermediate Similarity	NPC106895
0.8079	Intermediate Similarity	NPC217091
0.8068	Intermediate Similarity	NPC1173
0.8068	Intermediate Similarity	NPC158333
0.8068	Intermediate Similarity	NPC242262
0.8068	Intermediate Similarity	NPC472005
0.8068	Intermediate Similarity	NPC265395
0.8068	Intermediate Similarity	NPC473414
0.8068	Intermediate Similarity	NPC472022
0.8068	Intermediate Similarity	NPC256142
0.8068	Intermediate Similarity	NPC237549
0.8068	Intermediate Similarity	NPC472030
0.8068	Intermediate Similarity	NPC257213
0.8068	Intermediate Similarity	NPC304876
0.8068	Intermediate Similarity	NPC249471
0.8066	Intermediate Similarity	NPC471493
0.8057	Intermediate Similarity	NPC197037
0.8023	Intermediate Similarity	NPC114410
0.8023	Intermediate Similarity	NPC473670
0.8023	Intermediate Similarity	NPC282239
0.8023	Intermediate Similarity	NPC21410
0.8023	Intermediate Similarity	NPC112523
0.8	Intermediate Similarity	NPC91730
0.8	Intermediate Similarity	NPC7095
0.7966	Intermediate Similarity	NPC77719
0.7943	Intermediate Similarity	NPC250046
0.7943	Intermediate Similarity	NPC60509
0.7943	Intermediate Similarity	NPC81698
0.7933	Intermediate Similarity	NPC469771
0.7921	Intermediate Similarity	NPC472549
0.7901	Intermediate Similarity	NPC476077
0.7898	Intermediate Similarity	NPC198455
0.7898	Intermediate Similarity	NPC161239
0.7898	Intermediate Similarity	NPC112216
0.7898	Intermediate Similarity	NPC165260
0.7886	Intermediate Similarity	NPC217918
0.7853	Intermediate Similarity	NPC471103
0.7853	Intermediate Similarity	NPC306799
0.7853	Intermediate Similarity	NPC51602
0.7853	Intermediate Similarity	NPC470153
0.7853	Intermediate Similarity	NPC101043
0.7809	Intermediate Similarity	NPC477905
0.7809	Intermediate Similarity	NPC472548
0.7797	Intermediate Similarity	NPC473214
0.7797	Intermediate Similarity	NPC254558
0.7797	Intermediate Similarity	NPC470245
0.7771	Intermediate Similarity	NPC127857
0.774	Intermediate Similarity	NPC473215
0.774	Intermediate Similarity	NPC476975
0.7722	Intermediate Similarity	NPC132599
0.7722	Intermediate Similarity	NPC469730
0.7722	Intermediate Similarity	NPC473632
0.7722	Intermediate Similarity	NPC473611
0.7714	Intermediate Similarity	NPC38696
0.764	Intermediate Similarity	NPC471101
0.764	Intermediate Similarity	NPC266265
0.764	Intermediate Similarity	NPC301556
0.764	Intermediate Similarity	NPC270590
0.764	Intermediate Similarity	NPC92293
0.7627	Intermediate Similarity	NPC474935
0.76	Intermediate Similarity	NPC182869
0.76	Intermediate Similarity	NPC34012
0.7584	Intermediate Similarity	NPC281717
0.7571	Intermediate Similarity	NPC472556
0.7571	Intermediate Similarity	NPC96903
0.7571	Intermediate Similarity	NPC174982
0.7571	Intermediate Similarity	NPC473088
0.7571	Intermediate Similarity	NPC277053
0.7571	Intermediate Similarity	NPC472568
0.7571	Intermediate Similarity	NPC200471
0.7571	Intermediate Similarity	NPC472575
0.7571	Intermediate Similarity	NPC177940
0.7571	Intermediate Similarity	NPC469349
0.7571	Intermediate Similarity	NPC184817
0.7571	Intermediate Similarity	NPC471107
0.7571	Intermediate Similarity	NPC471100
0.7571	Intermediate Similarity	NPC472571
0.7571	Intermediate Similarity	NPC476973
0.7571	Intermediate Similarity	NPC158663
0.7571	Intermediate Similarity	NPC470159
0.7571	Intermediate Similarity	NPC70403
0.7571	Intermediate Similarity	NPC301946
0.7571	Intermediate Similarity	NPC471104
0.7571	Intermediate Similarity	NPC472572
0.7571	Intermediate Similarity	NPC470157
0.7571	Intermediate Similarity	NPC171525
0.7571	Intermediate Similarity	NPC29704
0.7553	Intermediate Similarity	NPC102465
0.754	Intermediate Similarity	NPC30171
0.7537	Intermediate Similarity	NPC314941
0.7527	Intermediate Similarity	NPC150893
0.7527	Intermediate Similarity	NPC329960
0.7527	Intermediate Similarity	NPC295408
0.7514	Intermediate Similarity	NPC472573
0.7514	Intermediate Similarity	NPC241951
0.7514	Intermediate Similarity	NPC80895
0.7514	Intermediate Similarity	NPC188865
0.7514	Intermediate Similarity	NPC95265
0.7514	Intermediate Similarity	NPC475122
0.7514	Intermediate Similarity	NPC471912
0.7514	Intermediate Similarity	NPC25768
0.7514	Intermediate Similarity	NPC470231
0.7514	Intermediate Similarity	NPC11685
0.7514	Intermediate Similarity	NPC472569
0.7514	Intermediate Similarity	NPC70716
0.7514	Intermediate Similarity	NPC125106
0.7514	Intermediate Similarity	NPC95810
0.7514	Intermediate Similarity	NPC470152
0.7514	Intermediate Similarity	NPC475759
0.7514	Intermediate Similarity	NPC476974
0.7514	Intermediate Similarity	NPC57628
0.7514	Intermediate Similarity	NPC163719
0.7514	Intermediate Similarity	NPC472570
0.7513	Intermediate Similarity	NPC477471
0.7513	Intermediate Similarity	NPC278272
0.7513	Intermediate Similarity	NPC477466
0.7513	Intermediate Similarity	NPC120667
0.7513	Intermediate Similarity	NPC477469
0.7513	Intermediate Similarity	NPC477473
0.7512	Intermediate Similarity	NPC315889
0.75	Intermediate Similarity	NPC469399
0.7487	Intermediate Similarity	NPC471134
0.7486	Intermediate Similarity	NPC11410
0.7465	Intermediate Similarity	NPC96801
0.7465	Intermediate Similarity	NPC150698
0.7461	Intermediate Similarity	NPC475649
0.7458	Intermediate Similarity	NPC477894
0.7458	Intermediate Similarity	NPC163087
0.7446	Intermediate Similarity	NPC469417
0.7443	Intermediate Similarity	NPC213567
0.7433	Intermediate Similarity	NPC66193
0.7432	Intermediate Similarity	NPC251139
0.743	Intermediate Similarity	NPC94602
0.7429	Intermediate Similarity	NPC472371
0.7429	Intermediate Similarity	NPC472395
0.7409	Intermediate Similarity	NPC475345
0.7403	Intermediate Similarity	NPC31829
0.7401	Intermediate Similarity	NPC472546
0.7396	Intermediate Similarity	NPC469421
0.738	Intermediate Similarity	NPC253738
0.738	Intermediate Similarity	NPC55744
0.7376	Intermediate Similarity	NPC42286
0.7374	Intermediate Similarity	NPC473541
0.7368	Intermediate Similarity	NPC469420
0.7366	Intermediate Similarity	NPC475648
0.736	Intermediate Similarity	NPC191082
0.736	Intermediate Similarity	NPC177340
0.736	Intermediate Similarity	NPC246480
0.736	Intermediate Similarity	NPC473673
0.736	Intermediate Similarity	NPC475429
0.736	Intermediate Similarity	NPC270498
0.736	Intermediate Similarity	NPC139067
0.736	Intermediate Similarity	NPC147217
0.736	Intermediate Similarity	NPC477468
0.7354	Intermediate Similarity	NPC61891
0.7345	Intermediate Similarity	NPC291599
0.7345	Intermediate Similarity	NPC224491
0.7345	Intermediate Similarity	NPC87448
0.7345	Intermediate Similarity	NPC41481

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 NPC473558 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	558
0.2-0.3	1030
0.3-0.4	2378
0.4-0.5	3367
0.5-0.6	1418
0.6-0.7	188
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
0.9775	High Similarity	NPD8486	Clinical (unspecified phase)
0.9379	High Similarity	NPD8360	Approved
0.9379	High Similarity	NPD8361	Approved
0.9379	High Similarity	NPD8435	Approved
0.905	High Similarity	NPD8424	Clinical (unspecified phase)
0.8771	High Similarity	NPD8368	Discontinued
0.8729	High Similarity	NPD8407	Phase 2
0.8398	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.8241	Intermediate Similarity	NPD8462	Phase 1
0.8168	Intermediate Similarity	NPD8404	Phase 2
0.7577	Intermediate Similarity	NPD8150	Discontinued
0.7537	Intermediate Similarity	NPD8319	Approved
0.7537	Intermediate Similarity	NPD8320	Phase 1
0.7524	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD7874	Approved
0.7418	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD7801	Approved
0.7398	Intermediate Similarity	NPD8434	Phase 2
0.7327	Intermediate Similarity	NPD7699	Phase 2
0.7327	Intermediate Similarity	NPD7700	Phase 2
0.7264	Intermediate Similarity	NPD6535	Approved
0.7264	Intermediate Similarity	NPD6534	Approved
0.7225	Intermediate Similarity	NPD8151	Discontinued
0.7198	Intermediate Similarity	NPD7871	Phase 2
0.7198	Intermediate Similarity	NPD7870	Phase 2
0.7177	Intermediate Similarity	NPD7701	Phase 2
0.715	Intermediate Similarity	NPD7697	Approved
0.715	Intermediate Similarity	NPD7696	Phase 3
0.715	Intermediate Similarity	NPD7698	Approved
0.7113	Intermediate Similarity	NPD7799	Discontinued
0.7101	Intermediate Similarity	NPD6823	Phase 2
0.7087	Intermediate Similarity	NPD6780	Approved
0.7087	Intermediate Similarity	NPD6776	Approved
0.7087	Intermediate Similarity	NPD6781	Approved
0.7087	Intermediate Similarity	NPD6778	Approved
0.7087	Intermediate Similarity	NPD6777	Approved
0.7087	Intermediate Similarity	NPD6779	Approved
0.7087	Intermediate Similarity	NPD6782	Approved
0.7067	Intermediate Similarity	NPD7435	Discontinued
0.7056	Intermediate Similarity	NPD5030	Phase 2
0.7033	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4955	Approved
0.702	Intermediate Similarity	NPD4954	Approved
0.702	Intermediate Similarity	NPD5026	Approved
0.702	Intermediate Similarity	NPD5028	Approved
0.702	Intermediate Similarity	NPD5034	Approved
0.702	Intermediate Similarity	NPD36	Approved
0.7	Intermediate Similarity	NPD8468	Phase 2
0.7	Intermediate Similarity	NPD5036	Approved
0.6995	Remote Similarity	NPD7236	Approved
0.6989	Remote Similarity	NPD7239	Suspended
0.6965	Remote Similarity	NPD5037	Approved
0.6965	Remote Similarity	NPD5038	Approved
0.6919	Remote Similarity	NPD3823	Discontinued
0.6912	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7783	Phase 2
0.6825	Remote Similarity	NPD7497	Discontinued
0.6786	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8059	Phase 3
0.6738	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5035	Approved
0.6721	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5029	Approved
0.6716	Remote Similarity	NPD5031	Approved
0.6716	Remote Similarity	NPD5027	Approved
0.6699	Remote Similarity	NPD7282	Approved
0.6667	Remote Similarity	NPD5968	Phase 3
0.665	Remote Similarity	NPD6836	Approved
0.6637	Remote Similarity	NPD7907	Approved
0.6635	Remote Similarity	NPD6212	Phase 3
0.6635	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6213	Phase 3
0.6587	Remote Similarity	NPD3819	Phase 2
0.6585	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.657	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7058	Phase 2
0.6564	Remote Similarity	NPD7057	Phase 3
0.6557	Remote Similarity	NPD8285	Discontinued
0.6557	Remote Similarity	NPD7565	Approved
0.6557	Remote Similarity	NPD7811	Phase 3
0.6557	Remote Similarity	NPD7810	Phase 3
0.655	Remote Similarity	NPD8067	Phase 3
0.6546	Remote Similarity	NPD7972	Discontinued
0.6526	Remote Similarity	NPD4914	Approved
0.6524	Remote Similarity	NPD2575	Approved
0.651	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD8146	Phase 2
0.6489	Remote Similarity	NPD8366	Approved
0.6489	Remote Similarity	NPD6190	Approved
0.6488	Remote Similarity	NPD8312	Approved
0.6488	Remote Similarity	NPD8313	Approved
0.6473	Remote Similarity	NPD4665	Approved
0.6465	Remote Similarity	NPD6746	Phase 2
0.645	Remote Similarity	NPD5242	Approved
0.6447	Remote Similarity	NPD8491	Approved
0.6447	Remote Similarity	NPD7075	Discontinued
0.6439	Remote Similarity	NPD5032	Approved
0.6432	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD5544	Approved
0.64	Remote Similarity	NPD4111	Phase 1
0.6398	Remote Similarity	NPD4466	Phase 1
0.6393	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4387	Approved
0.6389	Remote Similarity	NPD4386	Approved
0.6386	Remote Similarity	NPD7473	Discontinued
0.6378	Remote Similarity	NPD7460	Discontinued
0.6378	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7930	Approved
0.6368	Remote Similarity	NPD3300	Phase 2
0.6355	Remote Similarity	NPD7177	Discontinued
0.6355	Remote Similarity	NPD3751	Discontinued
0.6349	Remote Similarity	NPD8166	Discontinued
0.6347	Remote Similarity	NPD7583	Approved
0.6345	Remote Similarity	NPD5402	Approved
0.6343	Remote Similarity	NPD3452	Approved
0.6343	Remote Similarity	NPD3450	Approved
0.6343	Remote Similarity	NPD2494	Approved
0.6343	Remote Similarity	NPD2493	Approved
0.6339	Remote Similarity	NPD7715	Approved
0.6339	Remote Similarity	NPD7713	Phase 3
0.6339	Remote Similarity	NPD7714	Approved
0.6337	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6166	Phase 2
0.6337	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4583	Approved
0.633	Remote Similarity	NPD4582	Approved
0.6327	Remote Similarity	NPD6801	Discontinued
0.6327	Remote Similarity	NPD7029	Discontinued
0.6326	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD5844	Phase 1
0.6324	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7654	Discontinued
0.6318	Remote Similarity	NPD7585	Approved
0.6308	Remote Similarity	NPD6599	Discontinued
0.6308	Remote Similarity	NPD2973	Approved
0.6308	Remote Similarity	NPD2975	Approved
0.6308	Remote Similarity	NPD2974	Approved
0.6301	Remote Similarity	NPD7999	Approved
0.6296	Remote Similarity	NPD4580	Approved
0.6293	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD4004	Approved
0.6284	Remote Similarity	NPD4002	Approved
0.628	Remote Similarity	NPD7962	Phase 2
0.6276	Remote Similarity	NPD6385	Approved
0.6276	Remote Similarity	NPD6386	Approved
0.6273	Remote Similarity	NPD7584	Approved
0.6271	Remote Similarity	NPD7048	Phase 3
0.6264	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD3400	Discontinued
0.6263	Remote Similarity	NPD4628	Phase 3
0.6262	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7458	Discontinued
0.6256	Remote Similarity	NPD3455	Phase 2
0.6256	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7961	Discontinued
0.625	Remote Similarity	NPD7546	Discontinued
0.6245	Remote Similarity	NPD6997	Phase 2
0.6239	Remote Similarity	NPD3057	Approved
0.6238	Remote Similarity	NPD7315	Approved
0.6238	Remote Similarity	NPD3787	Discontinued
0.6238	Remote Similarity	NPD6232	Discontinued
0.6237	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD6287	Discontinued
0.6233	Remote Similarity	NPD5676	Approved
0.6232	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD7038	Approved
0.6232	Remote Similarity	NPD7039	Approved
0.6231	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7008	Discontinued
0.623	Remote Similarity	NPD4738	Phase 2
0.6226	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6502	Phase 2
0.6224	Remote Similarity	NPD4380	Phase 2
0.6216	Remote Similarity	NPD5119	Approved
0.6216	Remote Similarity	NPD5121	Approved
0.6216	Remote Similarity	NPD5120	Approved
0.6215	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD8367	Approved
0.6212	Remote Similarity	NPD7819	Suspended
0.6209	Remote Similarity	NPD7693	Approved
0.6204	Remote Similarity	NPD4975	Approved
0.6204	Remote Similarity	NPD4974	Approved
0.6202	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD7808	Phase 3
0.6202	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.62	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD8461	Discontinued
0.6193	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD8127	Discontinued
0.6184	Remote Similarity	NPD7959	Clinical (unspecified phase)

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