NPASS Compound

Structure

CID171204 OpenBabel06191715542D 21 22 0 0 1 0 0 0 0 0999 V2000 -4.5493 -2.0255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0594 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 -2.5772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1211 -3.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0050 0.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2129 -0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2618 1.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 -1.8563 0.0000 C 0 0 0 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 -3.8061 -1.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2673 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1266 -3.4744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 -1.7518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 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 -1.7199 -4.3879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.6654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 11 2 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 20 1 1 0 0 0 15 9 1 6 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 12 1 6 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.15
Volume:	307.454
LogP:	2.507
LogD:	2.695
LogS:	-3.537
# Rotatable Bonds:	2
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	4.421
Fsp3:	0.529
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.714
MDCK Permeability:	4.465537494979799e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.966
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.588
Plasma Protein Binding (PPB):	86.84358978271484%
Volume Distribution (VD):	0.64
Pgp-substrate:	18.987449645996094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.253
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.188
CYP2C19-substrate:	0.171
CYP2C9-inhibitor:	0.256
CYP2C9-substrate:	0.117
CYP2D6-inhibitor:	0.106
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.294
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	5.995
Half-life (T1/2):	0.646

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.742
Drug-inuced Liver Injury (DILI):	0.751
AMES Toxicity:	0.134
Rat Oral Acute Toxicity:	0.61
Maximum Recommended Daily Dose:	0.134
Skin Sensitization:	0.864
Carcinogencity:	0.079
Eye Corrosion:	0.814
Eye Irritation:	0.215
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC171204

Natural Product ID:	NPC171204
*Common Name:**	Acetyl Neobritannilactone B
IUPAC Name:	[(3aR,4S,6E,10E,11aS)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] acetate
Synonyms:
Standard InCHIKey:	UPNVKIZABMRHNR-LFLWPQTJSA-N
Standard InCHI:	InChI=1S/C17H22O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h6,9,14-16H,3,5,7-8H2,1-2,4H3/b10-6+,11-9+/t14-,15-,16+/m0/s1
SMILES:	CC(=O)O[C@H]1C/C(=C/CC/C(=C/[C@H]2[C@@H]1C(=C)C(=O)O2)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520114
PubChem CID:	11962128
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides 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
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[16643020]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33264011]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO30983.1	Artemisia mexicana var. angustifolia	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14295	Ambrosia chamissonis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30761	Pyrethrum sp	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4652	Ambrosia dumosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14295	Ambrosia chamissonis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4652	Ambrosia dumosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15296	Pyrethrum sp.	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30983.1	Artemisia mexicana var. angustifolia	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26657	Conocephalum conicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12721	Liriodendron tulipifera	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14295	Ambrosia chamissonis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4652	Ambrosia dumosa	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
IC50	4
Others	20

Activity Type	# Activity
Cell Line	24

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	14700.0	nM	PMID[518283]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	57000.0	nM	PMID[518283]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	16200.0	nM	PMID[518283]
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	5400.0	nM	PMID[518283]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	15.47	%	PMID[518283]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	34.72	%	PMID[518283]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	76.87	%	PMID[518283]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	96.92	%	PMID[518283]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	98.66	%	PMID[518283]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	20.38	%	PMID[518283]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	47.56	%	PMID[518283]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	69.7	%	PMID[518283]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	81.43	%	PMID[518283]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	82.47	%	PMID[518283]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	22.93	%	PMID[518283]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	39.71	%	PMID[518283]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	95.17	%	PMID[518283]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	97.74	%	PMID[518283]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	98.05	%	PMID[518283]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	6.16	%	PMID[518283]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	9.89	%	PMID[518283]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	13.64	%	PMID[518283]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	43.11	%	PMID[518283]

☑ 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 NPC171204 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	185
0.1-0.2	1343
0.2-0.3	6106
0.3-0.4	15814
0.4-0.5	9802
0.5-0.6	6260
0.6-0.7	2377
0.7-0.8	627
0.8-0.85	80
0.85-0.9	72
0.9-0.95	25
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476028
1.0	High Similarity	NPC141789
0.9726	High Similarity	NPC270126
0.9595	High Similarity	NPC281132
0.9452	High Similarity	NPC97516
0.9437	High Similarity	NPC295633
0.9437	High Similarity	NPC58956
0.9437	High Similarity	NPC269206
0.9306	High Similarity	NPC140287
0.9306	High Similarity	NPC476355
0.9296	High Similarity	NPC163003
0.9221	High Similarity	NPC473390
0.9221	High Similarity	NPC169575
0.9221	High Similarity	NPC131669
0.9221	High Similarity	NPC40746
0.9211	High Similarity	NPC24417
0.92	High Similarity	NPC98557
0.92	High Similarity	NPC167881
0.9103	High Similarity	NPC158756
0.9103	High Similarity	NPC476804
0.9091	High Similarity	NPC229825
0.9054	High Similarity	NPC123360
0.9054	High Similarity	NPC235906
0.8987	High Similarity	NPC255307
0.8987	High Similarity	NPC470755
0.8974	High Similarity	NPC59097
0.8961	High Similarity	NPC281949
0.8961	High Similarity	NPC141810
0.8961	High Similarity	NPC301477
0.8961	High Similarity	NPC25684
0.8933	High Similarity	NPC474760
0.8919	High Similarity	NPC155587
0.8875	High Similarity	NPC475461
0.8875	High Similarity	NPC305475
0.8875	High Similarity	NPC469910
0.8875	High Similarity	NPC50637
0.8861	High Similarity	NPC96259
0.8861	High Similarity	NPC141193
0.8861	High Similarity	NPC191476
0.8861	High Similarity	NPC114979
0.8816	High Similarity	NPC471465
0.8816	High Similarity	NPC196653
0.8816	High Similarity	NPC93763
0.8816	High Similarity	NPC108816
0.8767	High Similarity	NPC129665
0.8765	High Similarity	NPC266957
0.8734	High Similarity	NPC474703
0.8732	High Similarity	NPC194871
0.8718	High Similarity	NPC52861
0.8701	High Similarity	NPC178277
0.8701	High Similarity	NPC617
0.8684	High Similarity	NPC320630
0.8684	High Similarity	NPC7563
0.8684	High Similarity	NPC476794
0.8684	High Similarity	NPC116177
0.8684	High Similarity	NPC470240
0.8659	High Similarity	NPC475819
0.8659	High Similarity	NPC476805
0.8659	High Similarity	NPC476803
0.8642	High Similarity	NPC150755
0.8571	High Similarity	NPC267231
0.8554	High Similarity	NPC166919
0.8553	High Similarity	NPC68819
0.85	High Similarity	NPC116543
0.8493	Intermediate Similarity	NPC88877
0.8493	Intermediate Similarity	NPC476591
0.8481	Intermediate Similarity	NPC471325
0.8452	Intermediate Similarity	NPC474232
0.8452	Intermediate Similarity	NPC469368
0.8452	Intermediate Similarity	NPC144133
0.8452	Intermediate Similarity	NPC179394
0.8452	Intermediate Similarity	NPC475855
0.8452	Intermediate Similarity	NPC473619
0.8442	Intermediate Similarity	NPC187568
0.8442	Intermediate Similarity	NPC57744
0.8442	Intermediate Similarity	NPC65603
0.8442	Intermediate Similarity	NPC41780
0.8434	Intermediate Similarity	NPC473715
0.8421	Intermediate Similarity	NPC138408
0.8421	Intermediate Similarity	NPC193351
0.8421	Intermediate Similarity	NPC226669
0.8415	Intermediate Similarity	NPC107787
0.8395	Intermediate Similarity	NPC115786
0.8395	Intermediate Similarity	NPC159635
0.8375	Intermediate Similarity	NPC173609
0.8356	Intermediate Similarity	NPC470256
0.8353	Intermediate Similarity	NPC473321
0.8333	Intermediate Similarity	NPC151770
0.8333	Intermediate Similarity	NPC128276
0.8293	Intermediate Similarity	NPC78089
0.8293	Intermediate Similarity	NPC165162
0.8272	Intermediate Similarity	NPC475947
0.8272	Intermediate Similarity	NPC318468
0.8256	Intermediate Similarity	NPC288240
0.8256	Intermediate Similarity	NPC162205
0.8256	Intermediate Similarity	NPC475302
0.8256	Intermediate Similarity	NPC125674
0.8256	Intermediate Similarity	NPC295204
0.8256	Intermediate Similarity	NPC228451
0.8256	Intermediate Similarity	NPC475838
0.8256	Intermediate Similarity	NPC165383
0.8256	Intermediate Similarity	NPC273579
0.8161	Intermediate Similarity	NPC473316
0.8161	Intermediate Similarity	NPC471147
0.8161	Intermediate Similarity	NPC473330
0.8161	Intermediate Similarity	NPC474247
0.8161	Intermediate Similarity	NPC140543
0.8148	Intermediate Similarity	NPC89555
0.8118	Intermediate Similarity	NPC474032
0.8095	Intermediate Similarity	NPC231889
0.8082	Intermediate Similarity	NPC248125
0.8072	Intermediate Similarity	NPC21469
0.8072	Intermediate Similarity	NPC215364
0.8072	Intermediate Similarity	NPC50362
0.8072	Intermediate Similarity	NPC38468
0.8072	Intermediate Similarity	NPC319795
0.8068	Intermediate Similarity	NPC475659
0.8068	Intermediate Similarity	NPC471141
0.8068	Intermediate Similarity	NPC471142
0.8068	Intermediate Similarity	NPC477922
0.8052	Intermediate Similarity	NPC48641
0.8052	Intermediate Similarity	NPC15499
0.8052	Intermediate Similarity	NPC474758
0.8052	Intermediate Similarity	NPC117746
0.8052	Intermediate Similarity	NPC294434
0.8052	Intermediate Similarity	NPC259599
0.8049	Intermediate Similarity	NPC170286
0.8049	Intermediate Similarity	NPC272814
0.8049	Intermediate Similarity	NPC250315
0.8025	Intermediate Similarity	NPC42470
0.8023	Intermediate Similarity	NPC80875
0.8023	Intermediate Similarity	NPC312042
0.8023	Intermediate Similarity	NPC475748
0.8	Intermediate Similarity	NPC182550
0.8	Intermediate Similarity	NPC472965
0.8	Intermediate Similarity	NPC264227
0.8	Intermediate Similarity	NPC89128
0.8	Intermediate Similarity	NPC470239
0.8	Intermediate Similarity	NPC470244
0.8	Intermediate Similarity	NPC63649
0.8	Intermediate Similarity	NPC19841
0.8	Intermediate Similarity	NPC477302
0.7978	Intermediate Similarity	NPC477921
0.7978	Intermediate Similarity	NPC17585
0.7978	Intermediate Similarity	NPC306041
0.7978	Intermediate Similarity	NPC473859
0.7978	Intermediate Similarity	NPC279621
0.7978	Intermediate Similarity	NPC230800
0.7976	Intermediate Similarity	NPC284902
0.7976	Intermediate Similarity	NPC469483
0.7955	Intermediate Similarity	NPC57405
0.7955	Intermediate Similarity	NPC303942
0.7955	Intermediate Similarity	NPC476267
0.7927	Intermediate Similarity	NPC35556
0.7927	Intermediate Similarity	NPC85772
0.7927	Intermediate Similarity	NPC475690
0.7907	Intermediate Similarity	NPC218927
0.7907	Intermediate Similarity	NPC206001
0.7901	Intermediate Similarity	NPC276356
0.7901	Intermediate Similarity	NPC302426
0.7901	Intermediate Similarity	NPC223904
0.7895	Intermediate Similarity	NPC472955
0.7895	Intermediate Similarity	NPC67183
0.7889	Intermediate Similarity	NPC471140
0.7882	Intermediate Similarity	NPC475703
0.7882	Intermediate Similarity	NPC160138
0.7875	Intermediate Similarity	NPC472960
0.7867	Intermediate Similarity	NPC218477
0.7841	Intermediate Similarity	NPC476300
0.7841	Intermediate Similarity	NPC475912
0.7831	Intermediate Similarity	NPC128429
0.7821	Intermediate Similarity	NPC114727
0.7821	Intermediate Similarity	NPC476590
0.7816	Intermediate Similarity	NPC51004
0.7816	Intermediate Similarity	NPC49342
0.7816	Intermediate Similarity	NPC251385
0.7816	Intermediate Similarity	NPC129419
0.7805	Intermediate Similarity	NPC325031
0.7805	Intermediate Similarity	NPC475481
0.7805	Intermediate Similarity	NPC39411
0.7805	Intermediate Similarity	NPC79277
0.7805	Intermediate Similarity	NPC255580
0.7802	Intermediate Similarity	NPC471144
0.7802	Intermediate Similarity	NPC279561
0.7792	Intermediate Similarity	NPC84038
0.7791	Intermediate Similarity	NPC136879
0.7791	Intermediate Similarity	NPC202672
0.7791	Intermediate Similarity	NPC475902
0.7778	Intermediate Similarity	NPC473980
0.7778	Intermediate Similarity	NPC473981
0.7765	Intermediate Similarity	NPC279859
0.7765	Intermediate Similarity	NPC38576
0.7765	Intermediate Similarity	NPC64153
0.7753	Intermediate Similarity	NPC476596
0.7753	Intermediate Similarity	NPC474338
0.7753	Intermediate Similarity	NPC477131
0.775	Intermediate Similarity	NPC10572
0.7727	Intermediate Similarity	NPC150978
0.7727	Intermediate Similarity	NPC30515
0.7727	Intermediate Similarity	NPC70595

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 NPC171204 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1918
0.2-0.3	4018
0.3-0.4	2129
0.4-0.5	629
0.5-0.6	223
0.6-0.7	52
0.7-0.8	11
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
0.8072	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1695	Approved
0.7294	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1694	Approved
0.7222	Intermediate Similarity	NPD6698	Approved
0.7222	Intermediate Similarity	NPD46	Approved
0.7209	Intermediate Similarity	NPD7154	Phase 3
0.7093	Intermediate Similarity	NPD5209	Approved
0.7059	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5785	Approved
0.7013	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8039	Approved
0.6854	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5363	Approved
0.6824	Remote Similarity	NPD4271	Approved
0.6824	Remote Similarity	NPD4268	Approved
0.6818	Remote Similarity	NPD5362	Discontinued
0.6778	Remote Similarity	NPD4249	Approved
0.6705	Remote Similarity	NPD4269	Approved
0.6705	Remote Similarity	NPD6435	Approved
0.6705	Remote Similarity	NPD4270	Approved
0.6703	Remote Similarity	NPD4250	Approved
0.6703	Remote Similarity	NPD4251	Approved
0.6701	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6596	Remote Similarity	NPD7983	Approved
0.6593	Remote Similarity	NPD5786	Approved
0.6591	Remote Similarity	NPD5369	Approved
0.6538	Remote Similarity	NPD6371	Approved
0.6477	Remote Similarity	NPD5368	Approved
0.6437	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6927	Phase 3
0.6364	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5778	Approved
0.6354	Remote Similarity	NPD6399	Phase 3
0.6354	Remote Similarity	NPD5779	Approved
0.6346	Remote Similarity	NPD6686	Approved
0.6322	Remote Similarity	NPD4756	Discovery
0.6321	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5282	Discontinued
0.6264	Remote Similarity	NPD5331	Approved
0.6264	Remote Similarity	NPD5332	Approved
0.6237	Remote Similarity	NPD6684	Approved
0.6237	Remote Similarity	NPD7334	Approved
0.6237	Remote Similarity	NPD6422	Discontinued
0.6237	Remote Similarity	NPD7521	Approved
0.6237	Remote Similarity	NPD7146	Approved
0.6237	Remote Similarity	NPD6409	Approved
0.6237	Remote Similarity	NPD5330	Approved
0.6222	Remote Similarity	NPD4790	Discontinued
0.6211	Remote Similarity	NPD5370	Suspended
0.6211	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6101	Approved
0.6196	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7839	Suspended
0.6122	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7900	Approved
0.6111	Remote Similarity	NPD6053	Discontinued
0.6105	Remote Similarity	NPD6903	Approved
0.6105	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5737	Approved
0.6105	Remote Similarity	NPD6672	Approved
0.6082	Remote Similarity	NPD5693	Phase 1
0.6082	Remote Similarity	NPD6411	Approved
0.6082	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD2067	Discontinued
0.604	Remote Similarity	NPD7638	Approved
0.6036	Remote Similarity	NPD7115	Discovery
0.6019	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6008	Approved
0.598	Remote Similarity	NPD7639	Approved
0.598	Remote Similarity	NPD6648	Approved
0.598	Remote Similarity	NPD7640	Approved
0.5946	Remote Similarity	NPD28	Approved
0.5946	Remote Similarity	NPD29	Approved
0.5943	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD7902	Approved
0.5922	Remote Similarity	NPD5344	Discontinued
0.5918	Remote Similarity	NPD7637	Suspended
0.5904	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5695	Phase 3
0.59	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5696	Approved
0.5876	Remote Similarity	NPD6051	Approved
0.5875	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3197	Phase 1
0.5854	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2182	Approved
0.5833	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD8513	Phase 3
0.5826	Remote Similarity	NPD8516	Approved
0.5826	Remote Similarity	NPD8515	Approved
0.5826	Remote Similarity	NPD8517	Approved
0.5816	Remote Similarity	NPD5207	Approved
0.58	Remote Similarity	NPD7748	Approved
0.5794	Remote Similarity	NPD5697	Approved
0.5789	Remote Similarity	NPD3172	Approved
0.5784	Remote Similarity	NPD6083	Phase 2
0.5784	Remote Similarity	NPD6084	Phase 2
0.578	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD5343	Approved
0.5741	Remote Similarity	NPD6881	Approved
0.5741	Remote Similarity	NPD6899	Approved
0.5732	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6649	Approved
0.5727	Remote Similarity	NPD2204	Approved
0.5727	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD3196	Approved
0.5714	Remote Similarity	NPD6673	Approved
0.5714	Remote Similarity	NPD7331	Phase 2
0.5714	Remote Similarity	NPD3195	Phase 2
0.5714	Remote Similarity	NPD9298	Approved
0.5714	Remote Similarity	NPD4266	Approved
0.5714	Remote Similarity	NPD6904	Approved
0.5714	Remote Similarity	NPD3194	Approved
0.5714	Remote Similarity	NPD6080	Approved
0.5701	Remote Similarity	NPD7128	Approved
0.5701	Remote Similarity	NPD6402	Approved
0.5701	Remote Similarity	NPD6675	Approved
0.5701	Remote Similarity	NPD5739	Approved
0.5694	Remote Similarity	NPD3174	Discontinued
0.5688	Remote Similarity	NPD6014	Approved
0.5688	Remote Similarity	NPD6373	Approved
0.5688	Remote Similarity	NPD6013	Approved
0.5688	Remote Similarity	NPD6372	Approved
0.5688	Remote Similarity	NPD6012	Approved
0.5688	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD3668	Phase 3
0.567	Remote Similarity	NPD3573	Approved
0.566	Remote Similarity	NPD6647	Phase 2
0.5657	Remote Similarity	NPD5692	Phase 3
0.5648	Remote Similarity	NPD5701	Approved
0.5644	Remote Similarity	NPD6001	Approved
0.5638	Remote Similarity	NPD3667	Approved
0.5636	Remote Similarity	NPD7102	Approved
0.5636	Remote Similarity	NPD6883	Approved
0.5636	Remote Similarity	NPD7290	Approved
0.5612	Remote Similarity	NPD5208	Approved
0.56	Remote Similarity	NPD7515	Phase 2
0.56	Remote Similarity	NPD5281	Approved
0.56	Remote Similarity	NPD8034	Phase 2
0.56	Remote Similarity	NPD5694	Approved
0.56	Remote Similarity	NPD8035	Phase 2
0.56	Remote Similarity	NPD5284	Approved
0.56	Remote Similarity	NPD6050	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