NPASS Compound

Structure

CID167635 OpenBabel06191715542D 36 43 0 0 1 0 0 0 0 0999 V2000 3.7646 0.2791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8353 3.0566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7201 -2.3776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8232 -1.4276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7198 -1.4261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6474 -0.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4238 -1.4269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5997 -0.9514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8962 -2.8535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -0.9515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1244 1.7744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1946 0.2169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9514 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6970 0.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0714 0.4764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5341 -0.9278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3002 1.2988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7752 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5887 -0.1964 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3004 2.2504 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6482 0.9506 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8955 0.0009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7754 0.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8957 -0.9506 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6480 -0.0009 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2477 -0.9510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1272 0.4753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5995 0.0001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1270 1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2475 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0718 -1.4265 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8243 0.4753 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9510 1.9028 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0721 -2.3780 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4234 0.4760 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3 5 1 0 0 0 0 3 9 1 0 0 0 0 4 6 1 0 0 0 0 4 10 1 0 0 0 0 5 24 1 0 0 0 0 6 25 1 0 0 0 0 7 8 1 0 0 0 0 7 26 1 0 0 0 0 8 28 1 0 0 0 0 9 34 1 0 0 0 0 10 35 1 0 0 0 0 11 20 1 0 0 0 0 12 19 1 0 0 0 0 13 23 2 0 0 0 0 13 27 1 0 0 0 0 14 21 1 0 0 0 0 14 29 1 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 23 1 0 0 0 0 18 33 2 0 0 0 0 19 1 1 6 0 0 0 20 2 1 1 0 0 0 21 11 1 1 0 0 0 21 25 1 0 0 0 0 22 12 1 6 0 0 0 22 24 1 0 0 0 0 24 31 1 1 0 0 0 25 32 1 1 0 0 0 26 30 1 0 0 0 0 26 31 1 6 0 0 0 27 29 2 0 0 0 0 27 32 1 0 0 0 0 28 23 1 1 0 0 0 28 36 1 0 0 0 0 29 33 1 0 0 0 0 30 15 1 6 0 0 0 30 36 1 0 0 0 0 31 16 1 6 0 0 0 31 34 1 0 0 0 0 32 17 1 1 0 0 0 32 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.39
Volume:	529.654
LogP:	4.384
LogD:	4.35
LogS:	-2.679
# Rotatable Bonds:	1
TPSA:	48.98
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.49
Synthetic Accessibility Score:	6.634
Fsp3:	0.844
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.672
MDCK Permeability:	1.8922457911685342e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.239
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	59.150390625%
Volume Distribution (VD):	0.869
Pgp-substrate:	32.39427185058594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.888
CYP2C19-inhibitor:	0.168
CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.267
CYP2D6-inhibitor:	0.813
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.656
CYP3A4-substrate:	0.681

ADMET: Excretion

Clearance (CL):	4.017
Half-life (T1/2):	0.179

ADMET: Toxicity

hERG Blockers:	0.843
Human Hepatotoxicity (H-HT):	0.962
Drug-inuced Liver Injury (DILI):	0.597
AMES Toxicity:	0.11
Rat Oral Acute Toxicity:	0.191
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.957
Carcinogencity:	0.008
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.695

Download Data

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

Natural Product: NPC167635

Natural Product ID:	NPC167635
*Common Name:**	Complanadine E
IUPAC Name:	n.a.
Synonyms:	Complanadine E
Standard InCHIKey:	IRZUNWKJFGYZDJ-RCMTYSEESA-N
Standard InCHI:	InChI=1S/C32H48N4/c1-19-12-22-15-30-26(31(16-19)24(22)5-3-9-34-31)7-8-28(36-30)23-13-27-29(33-18-23)14-21-11-20(2)17-32(27)25(21)6-4-10-35-32/h13,18-22,24-26,28,30,34-36H,3-12,14-17H2,1-2H3/t19-,20-,21+,22+,24-,25-,26-,28+,30-,31-,32-/m1/s1
SMILES:	C[C@@H]1C[C@H]2C[C@@H]3[C@@H](CC[C@@H](c4cc5c(C[C@@H]6C[C@@H](C)C[C@]75[C@@H]6CCCN7)nc4)N3)[C@@]3(C1)[C@@H]2CCCN3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644378
PubChem CID:	53320497
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO19825	Litsea japonica	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[14575444]
NPO16934	Nephthea chabrolii	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16309317]
NPO7688	Artemisia selengensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19076	Gaillardia pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19364	Aconitum chasmanthum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19364	Aconitum chasmanthum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19076	Gaillardia pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19076	Gaillardia pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18023	Vitex quinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21360	Cordia corymbosa	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19076	Gaillardia pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19869	Fusicolla aquaeductuum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19565	Crocus chrysanthus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15450	Minuria leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19364	Aconitum chasmanthum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16934	Nephthea chabrolii	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18518	Haematomma nemetzii	Species	Haematommataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19825	Litsea japonica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18499	Podium complanatum	Species	Sphecidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11060	Doris luteorosea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9799	Hebeloma longicaudum	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17577	Azalea ovata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19234	Hymenopappus newberryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19298	Gerbera crocea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17341	Gambeya africana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7688	Artemisia selengensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17887	Penstemon centranthifolius	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19696	Othonna quercifolia	Species	Asteraceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2624	Individual Protein	Beta-nerve growth factor	Homo sapiens	FC	=	2.8	n.a.	PMID[551625]

☑ 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 NPC167635 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	959
0.1-0.2	7532
0.2-0.3	22966
0.3-0.4	6121
0.4-0.5	2647
0.5-0.6	1822
0.6-0.7	586
0.7-0.8	58
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9595	High Similarity	NPC193740
0.929	High Similarity	NPC201634
0.8182	Intermediate Similarity	NPC34837
0.7963	Intermediate Similarity	NPC56765
0.777	Intermediate Similarity	NPC166424
0.777	Intermediate Similarity	NPC245244
0.777	Intermediate Similarity	NPC146373
0.7744	Intermediate Similarity	NPC206819
0.7744	Intermediate Similarity	NPC318065
0.7744	Intermediate Similarity	NPC41257
0.7576	Intermediate Similarity	NPC286427
0.7568	Intermediate Similarity	NPC329825
0.7564	Intermediate Similarity	NPC314102
0.7564	Intermediate Similarity	NPC251722
0.7558	Intermediate Similarity	NPC280852
0.753	Intermediate Similarity	NPC474880
0.753	Intermediate Similarity	NPC221786
0.75	Intermediate Similarity	NPC297034
0.75	Intermediate Similarity	NPC90723
0.7485	Intermediate Similarity	NPC44773
0.7485	Intermediate Similarity	NPC215584
0.7484	Intermediate Similarity	NPC469766
0.7439	Intermediate Similarity	NPC470233
0.7427	Intermediate Similarity	NPC474897
0.7421	Intermediate Similarity	NPC469784
0.7421	Intermediate Similarity	NPC469783
0.7421	Intermediate Similarity	NPC469761
0.7421	Intermediate Similarity	NPC469768
0.7421	Intermediate Similarity	NPC469780
0.7421	Intermediate Similarity	NPC469767
0.7421	Intermediate Similarity	NPC469779
0.7405	Intermediate Similarity	NPC169433
0.7403	Intermediate Similarity	NPC282398
0.7403	Intermediate Similarity	NPC69914
0.7396	Intermediate Similarity	NPC78375
0.7396	Intermediate Similarity	NPC476446
0.7396	Intermediate Similarity	NPC469813
0.7381	Intermediate Similarity	NPC229173
0.7378	Intermediate Similarity	NPC33421
0.7362	Intermediate Similarity	NPC21605
0.7351	Intermediate Similarity	NPC27740
0.7338	Intermediate Similarity	NPC475090
0.7338	Intermediate Similarity	NPC329896
0.7338	Intermediate Similarity	NPC476131
0.7338	Intermediate Similarity	NPC475105
0.7326	Intermediate Similarity	NPC194411
0.7321	Intermediate Similarity	NPC475990
0.7305	Intermediate Similarity	NPC51054
0.7273	Intermediate Similarity	NPC40070
0.7273	Intermediate Similarity	NPC53947
0.7273	Intermediate Similarity	NPC89490
0.725	Intermediate Similarity	NPC73767
0.725	Intermediate Similarity	NPC110126
0.7244	Intermediate Similarity	NPC101165
0.7237	Intermediate Similarity	NPC476322
0.7233	Intermediate Similarity	NPC84911
0.7233	Intermediate Similarity	NPC105127
0.72	Intermediate Similarity	NPC37423
0.72	Intermediate Similarity	NPC275305
0.7186	Intermediate Similarity	NPC325903
0.7175	Intermediate Similarity	NPC176199
0.7175	Intermediate Similarity	NPC215795
0.717	Intermediate Similarity	NPC29886
0.717	Intermediate Similarity	NPC96102
0.717	Intermediate Similarity	NPC261195
0.716	Intermediate Similarity	NPC216643
0.7152	Intermediate Similarity	NPC477974
0.7143	Intermediate Similarity	NPC316811
0.7143	Intermediate Similarity	NPC315348
0.7143	Intermediate Similarity	NPC32002
0.7119	Intermediate Similarity	NPC68354
0.711	Intermediate Similarity	NPC98187
0.7108	Intermediate Similarity	NPC321911
0.7101	Intermediate Similarity	NPC476464
0.7091	Intermediate Similarity	NPC288838
0.7079	Intermediate Similarity	NPC232340
0.7067	Intermediate Similarity	NPC91958
0.7066	Intermediate Similarity	NPC206592
0.7066	Intermediate Similarity	NPC105818
0.7066	Intermediate Similarity	NPC24678
0.7059	Intermediate Similarity	NPC46358
0.7059	Intermediate Similarity	NPC290094
0.7055	Intermediate Similarity	NPC473868
0.7055	Intermediate Similarity	NPC63157
0.7055	Intermediate Similarity	NPC476454
0.7048	Intermediate Similarity	NPC201380
0.7048	Intermediate Similarity	NPC179787
0.7048	Intermediate Similarity	NPC469811
0.7041	Intermediate Similarity	NPC80597
0.7041	Intermediate Similarity	NPC211572
0.7041	Intermediate Similarity	NPC70922
0.7041	Intermediate Similarity	NPC75540
0.7041	Intermediate Similarity	NPC212376
0.7039	Intermediate Similarity	NPC48564
0.7039	Intermediate Similarity	NPC265605
0.7039	Intermediate Similarity	NPC182570
0.7037	Intermediate Similarity	NPC88097
0.703	Intermediate Similarity	NPC314372
0.703	Intermediate Similarity	NPC86288
0.7025	Intermediate Similarity	NPC471322
0.7021	Intermediate Similarity	NPC265576
0.7017	Intermediate Similarity	NPC467063
0.7012	Intermediate Similarity	NPC190296
0.7012	Intermediate Similarity	NPC20144
0.7011	Intermediate Similarity	NPC95783
0.7	Intermediate Similarity	NPC240136
0.7	Intermediate Similarity	NPC471402
0.7	Intermediate Similarity	NPC297486
0.6994	Remote Similarity	NPC317105
0.6994	Remote Similarity	NPC59084
0.6994	Remote Similarity	NPC279081
0.6988	Remote Similarity	NPC143872
0.6988	Remote Similarity	NPC63545
0.6982	Remote Similarity	NPC259644
0.6982	Remote Similarity	NPC469786
0.6982	Remote Similarity	NPC73952
0.6982	Remote Similarity	NPC469765
0.6982	Remote Similarity	NPC25008
0.6982	Remote Similarity	NPC469763
0.6982	Remote Similarity	NPC469760
0.6971	Remote Similarity	NPC201700
0.6959	Remote Similarity	NPC469897
0.6957	Remote Similarity	NPC325252
0.6954	Remote Similarity	NPC143603
0.6946	Remote Similarity	NPC477134
0.6944	Remote Similarity	NPC300688
0.6941	Remote Similarity	NPC476219
0.6936	Remote Similarity	NPC470203
0.6927	Remote Similarity	NPC237188
0.6923	Remote Similarity	NPC202957
0.6923	Remote Similarity	NPC169625
0.6918	Remote Similarity	NPC82295
0.6914	Remote Similarity	NPC150259
0.6914	Remote Similarity	NPC160105
0.6909	Remote Similarity	NPC477977
0.689	Remote Similarity	NPC230002
0.6879	Remote Similarity	NPC470204
0.6879	Remote Similarity	NPC122141
0.6872	Remote Similarity	NPC87755
0.6872	Remote Similarity	NPC474958
0.6854	Remote Similarity	NPC314603
0.6854	Remote Similarity	NPC259545
0.6845	Remote Similarity	NPC471957
0.6845	Remote Similarity	NPC470111
0.6833	Remote Similarity	NPC151939
0.6826	Remote Similarity	NPC159856
0.6821	Remote Similarity	NPC135141
0.6821	Remote Similarity	NPC476566
0.6821	Remote Similarity	NPC92796
0.6818	Remote Similarity	NPC49954
0.6818	Remote Similarity	NPC474561
0.6813	Remote Similarity	NPC256893
0.6802	Remote Similarity	NPC469785
0.6802	Remote Similarity	NPC475422
0.6802	Remote Similarity	NPC126066
0.68	Remote Similarity	NPC194640
0.6795	Remote Similarity	NPC122718
0.679	Remote Similarity	NPC198988
0.6788	Remote Similarity	NPC2949
0.6784	Remote Similarity	NPC475602
0.6784	Remote Similarity	NPC138842
0.6784	Remote Similarity	NPC200214
0.678	Remote Similarity	NPC63751
0.6778	Remote Similarity	NPC203754
0.6778	Remote Similarity	NPC150048
0.6772	Remote Similarity	NPC471313
0.6772	Remote Similarity	NPC471311
0.6769	Remote Similarity	NPC475288
0.6763	Remote Similarity	NPC236711
0.6763	Remote Similarity	NPC469762
0.676	Remote Similarity	NPC477611
0.676	Remote Similarity	NPC477976
0.6757	Remote Similarity	NPC27802
0.6755	Remote Similarity	NPC316359
0.6755	Remote Similarity	NPC315617
0.6743	Remote Similarity	NPC225018
0.6738	Remote Similarity	NPC231536
0.6727	Remote Similarity	NPC312092
0.6726	Remote Similarity	NPC204141
0.6725	Remote Similarity	NPC470823
0.6724	Remote Similarity	NPC6436
0.6722	Remote Similarity	NPC471579
0.6716	Remote Similarity	NPC251936
0.6708	Remote Similarity	NPC475450
0.6705	Remote Similarity	NPC311276
0.6705	Remote Similarity	NPC159319
0.6687	Remote Similarity	NPC115611
0.6686	Remote Similarity	NPC141926
0.6685	Remote Similarity	NPC70949
0.6684	Remote Similarity	NPC103119
0.6667	Remote Similarity	NPC477975
0.6667	Remote Similarity	NPC314058
0.6667	Remote Similarity	NPC472123
0.6667	Remote Similarity	NPC316018
0.6667	Remote Similarity	NPC473930
0.6667	Remote Similarity	NPC477042
0.6667	Remote Similarity	NPC471386
0.6667	Remote Similarity	NPC47190
0.6667	Remote Similarity	NPC81561
0.665	Remote Similarity	NPC175916

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 NPC167635 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	427
0.1-0.2	640
0.2-0.3	1358
0.3-0.4	2341
0.4-0.5	2508
0.5-0.6	1438
0.6-0.7	391
0.7-0.8	47
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
0.8037	Intermediate Similarity	NPD3323	Discontinued
0.7785	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD991	Phase 2
0.7784	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3942	Approved
0.7712	Intermediate Similarity	NPD3944	Approved
0.7667	Intermediate Similarity	NPD2119	Approved
0.7667	Intermediate Similarity	NPD2118	Approved
0.7588	Intermediate Similarity	NPD3610	Approved
0.7588	Intermediate Similarity	NPD3609	Approved
0.7516	Intermediate Similarity	NPD7469	Discontinued
0.7514	Intermediate Similarity	NPD4181	Approved
0.7484	Intermediate Similarity	NPD1722	Approved
0.7484	Intermediate Similarity	NPD4029	Approved
0.7484	Intermediate Similarity	NPD4030	Approved
0.7484	Intermediate Similarity	NPD4028	Approved
0.7469	Intermediate Similarity	NPD4547	Phase 3
0.7455	Intermediate Similarity	NPD975	Approved
0.7455	Intermediate Similarity	NPD976	Approved
0.7455	Intermediate Similarity	NPD977	Approved
0.744	Intermediate Similarity	NPD6771	Discontinued
0.744	Intermediate Similarity	NPD5315	Discontinued
0.7438	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3476	Approved
0.7403	Intermediate Similarity	NPD3475	Approved
0.7401	Intermediate Similarity	NPD7564	Discontinued
0.7394	Intermediate Similarity	NPD2837	Discontinued
0.7394	Intermediate Similarity	NPD3339	Approved
0.7358	Intermediate Similarity	NPD786	Approved
0.7329	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3100	Discontinued
0.7317	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1683	Approved
0.7278	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6497	Approved
0.7257	Intermediate Similarity	NPD4075	Phase 2
0.7257	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD9583	Approved
0.725	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD9392	Approved
0.723	Intermediate Similarity	NPD9396	Approved
0.7228	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5436	Phase 1
0.7219	Intermediate Similarity	NPD5787	Discontinued
0.72	Intermediate Similarity	NPD4128	Approved
0.7193	Intermediate Similarity	NPD3583	Phase 2
0.7182	Intermediate Similarity	NPD8431	Approved
0.7178	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2172	Phase 1
0.716	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7216	Approved
0.7143	Intermediate Similarity	NPD2068	Approved
0.7143	Intermediate Similarity	NPD2075	Approved
0.7143	Intermediate Similarity	NPD2070	Approved
0.7143	Intermediate Similarity	NPD2072	Approved
0.7143	Intermediate Similarity	NPD2071	Approved
0.7143	Intermediate Similarity	NPD2069	Approved
0.7143	Intermediate Similarity	NPD2074	Approved
0.7143	Intermediate Similarity	NPD7217	Approved
0.7143	Intermediate Similarity	NPD2073	Approved
0.7135	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD9357	Approved
0.7119	Intermediate Similarity	NPD7111	Discontinued
0.7119	Intermediate Similarity	NPD3505	Approved
0.7119	Intermediate Similarity	NPD3506	Approved
0.7118	Intermediate Similarity	NPD5418	Discontinued
0.7102	Intermediate Similarity	NPD3799	Suspended
0.7101	Intermediate Similarity	NPD3114	Approved
0.7101	Intermediate Similarity	NPD3112	Approved
0.7101	Intermediate Similarity	NPD3113	Approved
0.7101	Intermediate Similarity	NPD3115	Approved
0.7097	Intermediate Similarity	NPD1598	Discontinued
0.7095	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD3961	Discontinued
0.7086	Intermediate Similarity	NPD4811	Discontinued
0.7079	Intermediate Similarity	NPD4076	Approved
0.7079	Intermediate Similarity	NPD4079	Approved
0.707	Intermediate Similarity	NPD715	Phase 3
0.7069	Intermediate Similarity	NPD2641	Approved
0.7069	Intermediate Similarity	NPD2640	Approved
0.7063	Intermediate Similarity	NPD1255	Approved
0.7063	Intermediate Similarity	NPD1253	Approved
0.7063	Intermediate Similarity	NPD1254	Approved
0.7063	Intermediate Similarity	NPD1256	Approved
0.7059	Intermediate Similarity	NPD6664	Approved
0.7052	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4702	Approved
0.7048	Intermediate Similarity	NPD4703	Approved
0.7044	Intermediate Similarity	NPD3385	Approved
0.7041	Intermediate Similarity	NPD2165	Phase 1
0.7039	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD271	Approved
0.7039	Intermediate Similarity	NPD268	Approved
0.7024	Intermediate Similarity	NPD4641	Discontinued
0.7018	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2580	Discontinued
0.6993	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5254	Discontinued
0.6959	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD8026	Phase 1
0.6927	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5065	Approved
0.6909	Remote Similarity	NPD3717	Discontinued
0.6909	Remote Similarity	NPD2006	Phase 2
0.6905	Remote Similarity	NPD2430	Phase 2
0.6899	Remote Similarity	NPD947	Approved
0.6894	Remote Similarity	NPD4880	Discontinued
0.6882	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4639	Approved
0.6875	Remote Similarity	NPD4638	Approved
0.6875	Remote Similarity	NPD4640	Approved
0.6872	Remote Similarity	NPD6044	Discontinued
0.6865	Remote Similarity	NPD6363	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7175	Phase 1
0.6864	Remote Similarity	NPD2466	Phase 3
0.6864	Remote Similarity	NPD2462	Phase 3
0.6864	Remote Similarity	NPD2465	Approved
0.686	Remote Similarity	NPD2145	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6281	Approved
0.6821	Remote Similarity	NPD5255	Approved
0.6813	Remote Similarity	NPD803	Phase 1
0.6813	Remote Similarity	NPD1251	Discontinued
0.6811	Remote Similarity	NPD7394	Phase 2
0.6802	Remote Similarity	NPD2150	Discontinued
0.6796	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1404	Approved
0.6782	Remote Similarity	NPD1403	Approved
0.678	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5021	Discontinued
0.6778	Remote Similarity	NPD3348	Phase 2
0.6774	Remote Similarity	NPD7233	Approved
0.6774	Remote Similarity	NPD7234	Approved
0.677	Remote Similarity	NPD1993	Approved
0.677	Remote Similarity	NPD1994	Approved
0.677	Remote Similarity	NPD1995	Approved
0.6763	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.676	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD2481	Approved
0.6758	Remote Similarity	NPD2479	Phase 3
0.6743	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4024	Phase 3
0.6739	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6178	Phase 3
0.6723	Remote Similarity	NPD6446	Discontinued
0.6723	Remote Similarity	NPD3929	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD2642	Approved
0.6723	Remote Similarity	NPD2639	Approved
0.6722	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8408	Discontinued
0.6707	Remote Similarity	NPD4510	Discontinued
0.6705	Remote Similarity	NPD6026	Approved
0.6704	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6828	Phase 2
0.6704	Remote Similarity	NPD3117	Approved
0.6704	Remote Similarity	NPD3116	Approved
0.6687	Remote Similarity	NPD3654	Approved
0.6686	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5862	Discovery
0.6684	Remote Similarity	NPD7618	Phase 3
0.6684	Remote Similarity	NPD7957	Phase 1
0.6684	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7619	Phase 3
0.6684	Remote Similarity	NPD6068	Discontinued
0.6684	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7026	Phase 2
0.6667	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4824	Approved
0.6667	Remote Similarity	NPD3404	Approved
0.6667	Remote Similarity	NPD3813	Approved
0.6667	Remote Similarity	NPD4823	Approved
0.6667	Remote Similarity	NPD6595	Phase 3
0.6667	Remote Similarity	NPD1988	Phase 1
0.6667	Remote Similarity	NPD2720	Phase 1
0.6667	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4615	Phase 2
0.6649	Remote Similarity	NPD6133	Discontinued
0.6648	Remote Similarity	NPD8123	Approved
0.6648	Remote Similarity	NPD8122	Approved
0.6647	Remote Similarity	NPD6285	Phase 2
0.6646	Remote Similarity	NPD792	Discontinued
0.6646	Remote Similarity	NPD490	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD8020	Approved
0.6631	Remote Similarity	NPD8021	Approved
0.663	Remote Similarity	NPD7867	Phase 1
0.663	Remote Similarity	NPD4649	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