NPASS Compound

Structure

CID281132 OpenBabel06191716092D 26 27 0 0 1 0 0 0 0 0999 V2000 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9095 0.6338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 -4.3480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8765 -1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6685 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4697 -0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9309 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3321 -3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8116 1.2518 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 1.1174 1.6119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -4.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9254 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 0.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0649 -2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3267 -3.8052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3743 2.2811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2135 -4.7081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 1.9209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3217 -3.0608 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 11 2 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 15 1 0 0 0 0 7 14 1 0 0 0 0 7 16 1 0 0 0 0 8 15 2 0 0 0 0 9 14 1 0 0 0 0 9 20 2 0 0 0 0 10 15 1 0 0 0 0 10 24 1 0 0 0 0 11 19 1 0 0 0 0 12 21 2 0 0 0 0 12 24 1 0 0 0 0 13 22 2 0 0 0 0 13 25 1 0 0 0 0 16 18 1 0 0 0 0 16 25 1 6 0 0 0 17 8 1 6 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 11 1 1 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.14
Volume:	363.144
LogP:	0.896
LogD:	1.296
LogS:	-2.682
# Rotatable Bonds:	6
TPSA:	95.97
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.247
Synthetic Accessibility Score:	4.751
Fsp3:	0.474
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.712
MDCK Permeability:	0.00010826710786204785
Pgp-inhibitor:	0.007
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.929
20% Bioavailability (F20%):	0.215
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.154
Plasma Protein Binding (PPB):	52.35810470581055%
Volume Distribution (VD):	0.455
Pgp-substrate:	57.18135070800781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	0.092
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.218
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	2.438
Half-life (T1/2):	0.947

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.821
AMES Toxicity:	0.925
Rat Oral Acute Toxicity:	0.614
Maximum Recommended Daily Dose:	0.081
Skin Sensitization:	0.646
Carcinogencity:	0.55
Eye Corrosion:	0.257
Eye Irritation:	0.045
Respiratory Toxicity:	0.781

Download Data

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

Natural Product: NPC281132

Natural Product ID:	NPC281132
*Common Name:**	(6S,7R,8S)-8,15-Diacetoxy-14-Oxomelampa-1(10),4,11(13)-Trien-12,6-Olide
IUPAC Name:	[(3aR,4S,6E,10Z,11aR)-4-acetyloxy-6-formyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-10-yl]methyl acetate
Synonyms:
Standard InCHIKey:	SNYUMMZVPJTQOU-KJYAUEFBSA-N
Standard InCHI:	InChI=1S/C19H22O7/c1-11-18-16(25-13(3)22)7-14(9-20)5-4-6-15(10-24-12(2)21)8-17(18)26-19(11)23/h5,8-9,16-18H,1,4,6-7,10H2,2-3H3/b14-5+,15-8-/t16-,17+,18+/m0/s1
SMILES:	C=C1[C@@H]2[C@H](C/C(=CCC/C(=C/[C@H]2OC1=O)/COC(=O)C)/C=O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481827
PubChem CID:	10428712
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
NPO25689	Mikania minima	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10757707]
NPO23784	Botryosphaeria rhodina	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17432876]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24170571]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24170571]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[300080]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	Europe PMC[300080]
NPO429	Chrysosporium merdarium	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[9207909]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO429	Chrysosporium merdarium	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7685	Ormosia indurata	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO533	Heterophragma adenophyllum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5671	Streptomyces davawensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25689	Mikania minima	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23784	Botryosphaeria rhodina	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9890	Pleurobranchus membranaceus	Species	Pleurobranchidae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	1400.0	nM	PMID[475355]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2800.0	nM	PMID[475355]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	2800.0	nM	PMID[475355]

☑ 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 NPC281132 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	193
0.1-0.2	1412
0.2-0.3	6356
0.3-0.4	15699
0.4-0.5	9997
0.5-0.6	6061
0.6-0.7	2249
0.7-0.8	571
0.8-0.85	80
0.85-0.9	57
0.9-0.95	17
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC270126
0.9595	High Similarity	NPC476028
0.9595	High Similarity	NPC171204
0.9595	High Similarity	NPC141789
0.9359	High Similarity	NPC59097
0.9189	High Similarity	NPC476355
0.9114	High Similarity	NPC169575
0.9114	High Similarity	NPC40746
0.9079	High Similarity	NPC97516
0.9054	High Similarity	NPC269206
0.9054	High Similarity	NPC58956
0.9054	High Similarity	NPC295633
0.9012	High Similarity	NPC150755
0.8947	High Similarity	NPC123360
0.8933	High Similarity	NPC140287
0.8919	High Similarity	NPC163003
0.8889	High Similarity	NPC470755
0.8875	High Similarity	NPC131669
0.8875	High Similarity	NPC473390
0.8861	High Similarity	NPC24417
0.8846	High Similarity	NPC167881
0.8846	High Similarity	NPC98557
0.878	High Similarity	NPC305475
0.878	High Similarity	NPC475461
0.8765	High Similarity	NPC476804
0.8765	High Similarity	NPC158756
0.875	High Similarity	NPC229825
0.8718	High Similarity	NPC108816
0.8718	High Similarity	NPC93763
0.8701	High Similarity	NPC235906
0.8659	High Similarity	NPC255307
0.8625	High Similarity	NPC25684
0.8625	High Similarity	NPC301477
0.8625	High Similarity	NPC281949
0.8625	High Similarity	NPC141810
0.8608	High Similarity	NPC178277
0.859	High Similarity	NPC474760
0.8571	High Similarity	NPC476805
0.8571	High Similarity	NPC155587
0.8571	High Similarity	NPC475819
0.8554	High Similarity	NPC50637
0.8554	High Similarity	NPC469910
0.8537	High Similarity	NPC141193
0.8537	High Similarity	NPC114979
0.8537	High Similarity	NPC96259
0.8537	High Similarity	NPC191476
0.8481	Intermediate Similarity	NPC471465
0.8481	Intermediate Similarity	NPC196653
0.8471	Intermediate Similarity	NPC166919
0.8452	Intermediate Similarity	NPC266957
0.8421	Intermediate Similarity	NPC129665
0.8415	Intermediate Similarity	NPC474703
0.8415	Intermediate Similarity	NPC116543
0.8409	Intermediate Similarity	NPC477922
0.84	Intermediate Similarity	NPC476591
0.84	Intermediate Similarity	NPC88877
0.8395	Intermediate Similarity	NPC471325
0.8395	Intermediate Similarity	NPC52861
0.8378	Intermediate Similarity	NPC194871
0.8375	Intermediate Similarity	NPC617
0.8372	Intermediate Similarity	NPC179394
0.8372	Intermediate Similarity	NPC473619
0.8372	Intermediate Similarity	NPC475855
0.8372	Intermediate Similarity	NPC144133
0.8354	Intermediate Similarity	NPC116177
0.8354	Intermediate Similarity	NPC41780
0.8354	Intermediate Similarity	NPC7563
0.8354	Intermediate Similarity	NPC476794
0.8354	Intermediate Similarity	NPC470240
0.8354	Intermediate Similarity	NPC320630
0.8354	Intermediate Similarity	NPC187568
0.8354	Intermediate Similarity	NPC57744
0.8353	Intermediate Similarity	NPC476803
0.8333	Intermediate Similarity	NPC107787
0.8315	Intermediate Similarity	NPC477921
0.8313	Intermediate Similarity	NPC115786
0.8293	Intermediate Similarity	NPC173609
0.8276	Intermediate Similarity	NPC473321
0.8267	Intermediate Similarity	NPC470256
0.825	Intermediate Similarity	NPC472960
0.825	Intermediate Similarity	NPC267231
0.825	Intermediate Similarity	NPC128276
0.8228	Intermediate Similarity	NPC68819
0.8214	Intermediate Similarity	NPC78089
0.8193	Intermediate Similarity	NPC475947
0.8182	Intermediate Similarity	NPC228451
0.8182	Intermediate Similarity	NPC273579
0.8182	Intermediate Similarity	NPC125674
0.8182	Intermediate Similarity	NPC295204
0.8182	Intermediate Similarity	NPC288240
0.8182	Intermediate Similarity	NPC475838
0.8182	Intermediate Similarity	NPC165383
0.8182	Intermediate Similarity	NPC162205
0.8161	Intermediate Similarity	NPC474232
0.8161	Intermediate Similarity	NPC469368
0.814	Intermediate Similarity	NPC473715
0.8125	Intermediate Similarity	NPC65603
0.8125	Intermediate Similarity	NPC10572
0.8101	Intermediate Similarity	NPC138408
0.8101	Intermediate Similarity	NPC193351
0.8101	Intermediate Similarity	NPC226669
0.8095	Intermediate Similarity	NPC159635
0.809	Intermediate Similarity	NPC474247
0.809	Intermediate Similarity	NPC473316
0.809	Intermediate Similarity	NPC473330
0.809	Intermediate Similarity	NPC140543
0.8046	Intermediate Similarity	NPC151770
0.8	Intermediate Similarity	NPC471142
0.8	Intermediate Similarity	NPC248125
0.8	Intermediate Similarity	NPC215364
0.8	Intermediate Similarity	NPC471141
0.8	Intermediate Similarity	NPC165162
0.7978	Intermediate Similarity	NPC475302
0.7976	Intermediate Similarity	NPC318468
0.7975	Intermediate Similarity	NPC259599
0.7975	Intermediate Similarity	NPC474758
0.7975	Intermediate Similarity	NPC15499
0.7975	Intermediate Similarity	NPC117746
0.7975	Intermediate Similarity	NPC294434
0.7955	Intermediate Similarity	NPC312042
0.7952	Intermediate Similarity	NPC42470
0.7927	Intermediate Similarity	NPC472965
0.7927	Intermediate Similarity	NPC63649
0.7927	Intermediate Similarity	NPC264227
0.7912	Intermediate Similarity	NPC279621
0.7912	Intermediate Similarity	NPC230800
0.7912	Intermediate Similarity	NPC17585
0.7907	Intermediate Similarity	NPC469483
0.7907	Intermediate Similarity	NPC284902
0.7889	Intermediate Similarity	NPC471147
0.7889	Intermediate Similarity	NPC476267
0.7857	Intermediate Similarity	NPC35556
0.7857	Intermediate Similarity	NPC475690
0.7857	Intermediate Similarity	NPC85772
0.7857	Intermediate Similarity	NPC89555
0.7841	Intermediate Similarity	NPC474032
0.7831	Intermediate Similarity	NPC223904
0.7831	Intermediate Similarity	NPC302426
0.7821	Intermediate Similarity	NPC67183
0.7816	Intermediate Similarity	NPC475703
0.7816	Intermediate Similarity	NPC231889
0.7816	Intermediate Similarity	NPC160138
0.7802	Intermediate Similarity	NPC475659
0.7792	Intermediate Similarity	NPC218477
0.7791	Intermediate Similarity	NPC319795
0.7791	Intermediate Similarity	NPC38468
0.7791	Intermediate Similarity	NPC21469
0.7791	Intermediate Similarity	NPC50362
0.7778	Intermediate Similarity	NPC472959
0.7765	Intermediate Similarity	NPC170286
0.7765	Intermediate Similarity	NPC250315
0.7765	Intermediate Similarity	NPC272814
0.7753	Intermediate Similarity	NPC475748
0.7753	Intermediate Similarity	NPC129419
0.7753	Intermediate Similarity	NPC80875
0.7753	Intermediate Similarity	NPC49342
0.7753	Intermediate Similarity	NPC251385
0.775	Intermediate Similarity	NPC476590
0.775	Intermediate Similarity	NPC114727
0.775	Intermediate Similarity	NPC48641
0.7742	Intermediate Similarity	NPC471144
0.7738	Intermediate Similarity	NPC39411
0.7738	Intermediate Similarity	NPC325031
0.7738	Intermediate Similarity	NPC255580
0.7727	Intermediate Similarity	NPC477302
0.7727	Intermediate Similarity	NPC471057
0.7727	Intermediate Similarity	NPC475902
0.7727	Intermediate Similarity	NPC471058
0.7722	Intermediate Similarity	NPC84038
0.7717	Intermediate Similarity	NPC306041
0.7717	Intermediate Similarity	NPC473859
0.7711	Intermediate Similarity	NPC470239
0.7711	Intermediate Similarity	NPC473980
0.7711	Intermediate Similarity	NPC89128
0.7711	Intermediate Similarity	NPC19841
0.7711	Intermediate Similarity	NPC182550
0.7711	Intermediate Similarity	NPC473981
0.7711	Intermediate Similarity	NPC470244
0.7701	Intermediate Similarity	NPC64153
0.7701	Intermediate Similarity	NPC279859
0.7701	Intermediate Similarity	NPC38576
0.7692	Intermediate Similarity	NPC474338
0.7692	Intermediate Similarity	NPC476596
0.7692	Intermediate Similarity	NPC57405
0.7692	Intermediate Similarity	NPC303942
0.7692	Intermediate Similarity	NPC477131
0.7683	Intermediate Similarity	NPC68156
0.7667	Intermediate Similarity	NPC150978
0.7667	Intermediate Similarity	NPC74103
0.7667	Intermediate Similarity	NPC123177
0.7667	Intermediate Similarity	NPC284185
0.7667	Intermediate Similarity	NPC70595
0.766	Intermediate Similarity	NPC477512
0.766	Intermediate Similarity	NPC288876
0.7654	Intermediate Similarity	NPC329852
0.7654	Intermediate Similarity	NPC244166
0.764	Intermediate Similarity	NPC268298
0.764	Intermediate Similarity	NPC206001
0.764	Intermediate Similarity	NPC295312
0.764	Intermediate Similarity	NPC475971

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 NPC281132 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	2002
0.2-0.3	4026
0.3-0.4	2083
0.4-0.5	590
0.5-0.6	215
0.6-0.7	47
0.7-0.8	8
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
0.7791	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD1695	Approved
0.7241	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD1694	Approved
0.7174	Intermediate Similarity	NPD6698	Approved
0.7174	Intermediate Similarity	NPD46	Approved
0.7045	Intermediate Similarity	NPD5209	Approved
0.6989	Remote Similarity	NPD5785	Approved
0.6966	Remote Similarity	NPD7154	Phase 3
0.6962	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6632	Remote Similarity	NPD7838	Discovery
0.663	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD8039	Approved
0.6593	Remote Similarity	NPD5362	Discontinued
0.6591	Remote Similarity	NPD4268	Approved
0.6591	Remote Similarity	NPD4271	Approved
0.6559	Remote Similarity	NPD4249	Approved
0.6509	Remote Similarity	NPD6371	Approved
0.6489	Remote Similarity	NPD4250	Approved
0.6489	Remote Similarity	NPD4251	Approved
0.6484	Remote Similarity	NPD4270	Approved
0.6484	Remote Similarity	NPD4269	Approved
0.6484	Remote Similarity	NPD6435	Approved
0.6444	Remote Similarity	NPD4821	Approved
0.6444	Remote Similarity	NPD4822	Approved
0.6444	Remote Similarity	NPD4252	Approved
0.6444	Remote Similarity	NPD4819	Approved
0.6444	Remote Similarity	NPD4820	Approved
0.6392	Remote Similarity	NPD7983	Approved
0.6383	Remote Similarity	NPD5786	Approved
0.6374	Remote Similarity	NPD5369	Approved
0.6337	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6686	Approved
0.6292	Remote Similarity	NPD4756	Discovery
0.6264	Remote Similarity	NPD5368	Approved
0.6263	Remote Similarity	NPD5282	Discontinued
0.6222	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7334	Approved
0.6211	Remote Similarity	NPD5330	Approved
0.6211	Remote Similarity	NPD6684	Approved
0.6211	Remote Similarity	NPD7146	Approved
0.6211	Remote Similarity	NPD6409	Approved
0.6211	Remote Similarity	NPD7521	Approved
0.617	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5779	Approved
0.6162	Remote Similarity	NPD5778	Approved
0.6162	Remote Similarity	NPD6399	Phase 3
0.6147	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD6927	Phase 3
0.61	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7900	Approved
0.6091	Remote Similarity	NPD6053	Discontinued
0.6082	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD6903	Approved
0.6082	Remote Similarity	NPD5737	Approved
0.6082	Remote Similarity	NPD6672	Approved
0.6064	Remote Similarity	NPD5331	Approved
0.6064	Remote Similarity	NPD5332	Approved
0.6061	Remote Similarity	NPD5693	Phase 1
0.6055	Remote Similarity	NPD2067	Discontinued
0.6042	Remote Similarity	NPD6422	Discontinued
0.6022	Remote Similarity	NPD4790	Discontinued
0.602	Remote Similarity	NPD6101	Approved
0.602	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5370	Suspended
0.6019	Remote Similarity	NPD7638	Approved
0.6018	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6008	Approved
0.598	Remote Similarity	NPD7839	Suspended
0.5962	Remote Similarity	NPD6648	Approved
0.5962	Remote Similarity	NPD7640	Approved
0.5962	Remote Similarity	NPD7639	Approved
0.5926	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7902	Approved
0.5905	Remote Similarity	NPD5344	Discontinued
0.59	Remote Similarity	NPD6411	Approved
0.59	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5695	Phase 3
0.5882	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD5696	Approved
0.5818	Remote Similarity	NPD2182	Approved
0.58	Remote Similarity	NPD5207	Approved
0.5784	Remote Similarity	NPD7748	Approved
0.578	Remote Similarity	NPD5697	Approved
0.5769	Remote Similarity	NPD6083	Phase 2
0.5769	Remote Similarity	NPD6084	Phase 2
0.5766	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD7637	Suspended
0.5727	Remote Similarity	NPD6899	Approved
0.5727	Remote Similarity	NPD6881	Approved
0.5714	Remote Similarity	NPD29	Approved
0.5714	Remote Similarity	NPD28	Approved
0.5714	Remote Similarity	NPD7642	Approved
0.5714	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6649	Approved
0.5714	Remote Similarity	NPD6650	Approved
0.57	Remote Similarity	NPD6080	Approved
0.57	Remote Similarity	NPD6051	Approved
0.57	Remote Similarity	NPD6673	Approved
0.57	Remote Similarity	NPD6904	Approved
0.5698	Remote Similarity	NPD7331	Phase 2
0.569	Remote Similarity	NPD7641	Discontinued
0.5688	Remote Similarity	NPD5739	Approved
0.5688	Remote Similarity	NPD6402	Approved
0.5688	Remote Similarity	NPD6675	Approved
0.5688	Remote Similarity	NPD7128	Approved
0.5678	Remote Similarity	NPD8517	Approved
0.5678	Remote Similarity	NPD8513	Phase 3
0.5678	Remote Similarity	NPD8515	Approved
0.5678	Remote Similarity	NPD8516	Approved
0.5676	Remote Similarity	NPD6012	Approved
0.5676	Remote Similarity	NPD6014	Approved
0.5676	Remote Similarity	NPD6373	Approved
0.5676	Remote Similarity	NPD6372	Approved
0.5676	Remote Similarity	NPD6013	Approved
0.5676	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD3573	Approved
0.5648	Remote Similarity	NPD6647	Phase 2
0.5647	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD3197	Phase 1
0.5644	Remote Similarity	NPD5692	Phase 3
0.5636	Remote Similarity	NPD5701	Approved
0.5632	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD6001	Approved
0.5625	Remote Similarity	NPD6883	Approved
0.5625	Remote Similarity	NPD7290	Approved
0.5625	Remote Similarity	NPD7102	Approved
0.562	Remote Similarity	NPD7507	Approved
0.56	Remote Similarity	NPD5208	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