NPASS Compound

Structure

NPC11611 OpenBabel07101718222D 23 27 0 0 1 0 0 0 0 0999 V2000 3.3897 2.3605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0603 1.9621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8289 1.7246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5680 2.0543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1971 1.2313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4951 1.3916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1192 1.8568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0699 1.7465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0217 1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8516 -0.1705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9967 1.4410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5096 0.5826 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9321 0.9426 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6848 0.2225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6848 0.9426 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3085 -0.1375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4233 0.5826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3085 1.3027 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.1651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9321 0.2225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3085 -1.1375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4233 0.5826 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 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 6 1 0 0 0 0 6 13 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 12 5 1 6 0 0 0 13 18 1 6 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 6 0 0 0 14 23 1 0 0 0 0 15 18 1 6 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 16 21 2 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 2 1 6 0 0 0 19 3 1 1 0 0 0 20 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	330.155
LogP:	3.393
LogD:	3.097
LogS:	-4.912
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.506
Synthetic Accessibility Score:	5.976
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.84
MDCK Permeability:	2.4870401830412447e-05
Pgp-inhibitor:	0.029
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.069
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.724
Plasma Protein Binding (PPB):	82.66328430175781%
Volume Distribution (VD):	0.822
Pgp-substrate:	15.35456371307373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.527
CYP2C19-inhibitor:	0.198
CYP2C19-substrate:	0.798
CYP2C9-inhibitor:	0.165
CYP2C9-substrate:	0.119
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.505
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.38

ADMET: Excretion

Clearance (CL):	8.866
Half-life (T1/2):	0.313

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.296
Drug-inuced Liver Injury (DILI):	0.33
AMES Toxicity:	0.157
Rat Oral Acute Toxicity:	0.675
Maximum Recommended Daily Dose:	0.335
Skin Sensitization:	0.167
Carcinogencity:	0.852
Eye Corrosion:	0.882
Eye Irritation:	0.564
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC11611

Natural Product ID:	NPC11611
*Common Name:**	Mitrekaurenone
IUPAC Name:	n.a.
Synonyms:	Mitrekaurenone
Standard InCHIKey:	VCCKBMBRVGBEIV-UFUZVNNQSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-11-9-20-10-12(11)5-6-13(20)18(2)7-4-8-19(3)15(18)14(16(20)21)23-17(19)22/h12-15H,1,4-10H2,2-3H3/t12-,13+,14-,15+,18+,19-,20+/m1/s1
SMILES:	C=C1C[C@@]23C[C@H]1CC[C@H]3[C@]1([C@@H]3[C@H](C2=O)OC(=O)[C@]3(C)CCC1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079779
PubChem CID:	11381465
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO10501	Mitrephora glabra	Species	Annonaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[19874044]
NPO10501	Mitrephora glabra	Species	Annonaceae	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
MIC	4

Activity Type	# Activity
Cell Line	4
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[491644]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[491644]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	10000.0	nM	PMID[491644]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	10000.0	nM	PMID[491644]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	150.0	ug.mL-1	PMID[491644]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	38.0	ug.mL-1	PMID[491644]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	38.0	ug.mL-1	PMID[491644]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	38.0	ug.mL-1	PMID[491644]

☑ 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 NPC11611 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	248
0.1-0.2	1988
0.2-0.3	8317
0.3-0.4	14896
0.4-0.5	6168
0.5-0.6	6350
0.6-0.7	3946
0.7-0.8	762
0.8-0.85	18
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8523	High Similarity	NPC471042
0.8488	Intermediate Similarity	NPC476458
0.8488	Intermediate Similarity	NPC258153
0.8434	Intermediate Similarity	NPC92489
0.8295	Intermediate Similarity	NPC475509
0.8202	Intermediate Similarity	NPC98270
0.8182	Intermediate Similarity	NPC471037
0.8172	Intermediate Similarity	NPC294263
0.814	Intermediate Similarity	NPC471475
0.8065	Intermediate Similarity	NPC470230
0.8065	Intermediate Similarity	NPC250753
0.8046	Intermediate Similarity	NPC170038
0.8043	Intermediate Similarity	NPC471043
0.8021	Intermediate Similarity	NPC226986
0.8	Intermediate Similarity	NPC98639
0.8	Intermediate Similarity	NPC474971
0.8	Intermediate Similarity	NPC470223
0.7979	Intermediate Similarity	NPC470224
0.7959	Intermediate Similarity	NPC295276
0.7955	Intermediate Similarity	NPC475951
0.7938	Intermediate Similarity	NPC474724
0.7938	Intermediate Similarity	NPC109059
0.7938	Intermediate Similarity	NPC288
0.7935	Intermediate Similarity	NPC474719
0.7935	Intermediate Similarity	NPC28227
0.7935	Intermediate Similarity	NPC474845
0.7935	Intermediate Similarity	NPC4309
0.7931	Intermediate Similarity	NPC118987
0.7917	Intermediate Similarity	NPC200054
0.7917	Intermediate Similarity	NPC104568
0.7917	Intermediate Similarity	NPC470387
0.7917	Intermediate Similarity	NPC13949
0.7917	Intermediate Similarity	NPC29410
0.7912	Intermediate Similarity	NPC12774
0.7895	Intermediate Similarity	NPC475118
0.7895	Intermediate Similarity	NPC56525
0.7895	Intermediate Similarity	NPC303863
0.7889	Intermediate Similarity	NPC146683
0.7889	Intermediate Similarity	NPC239362
0.7872	Intermediate Similarity	NPC160506
0.7872	Intermediate Similarity	NPC198054
0.7865	Intermediate Similarity	NPC226988
0.7857	Intermediate Similarity	NPC279241
0.7835	Intermediate Similarity	NPC216904
0.7835	Intermediate Similarity	NPC10864
0.7835	Intermediate Similarity	NPC469810
0.7835	Intermediate Similarity	NPC23680
0.7826	Intermediate Similarity	NPC33768
0.7822	Intermediate Similarity	NPC50535
0.7816	Intermediate Similarity	NPC63020
0.7812	Intermediate Similarity	NPC210214
0.7812	Intermediate Similarity	NPC470232
0.7812	Intermediate Similarity	NPC266431
0.7812	Intermediate Similarity	NPC470229
0.7802	Intermediate Similarity	NPC294438
0.7802	Intermediate Similarity	NPC264317
0.78	Intermediate Similarity	NPC216114
0.78	Intermediate Similarity	NPC469985
0.7791	Intermediate Similarity	NPC471046
0.7789	Intermediate Similarity	NPC244356
0.7789	Intermediate Similarity	NPC224060
0.7789	Intermediate Similarity	NPC475700
0.7778	Intermediate Similarity	NPC118800
0.7778	Intermediate Similarity	NPC170862
0.7755	Intermediate Similarity	NPC28864
0.7755	Intermediate Similarity	NPC162459
0.7755	Intermediate Similarity	NPC112753
0.7755	Intermediate Similarity	NPC275439
0.7755	Intermediate Similarity	NPC38471
0.7755	Intermediate Similarity	NPC98837
0.7755	Intermediate Similarity	NPC89099
0.7755	Intermediate Similarity	NPC20479
0.7755	Intermediate Similarity	NPC38296
0.7755	Intermediate Similarity	NPC471038
0.7753	Intermediate Similarity	NPC223330
0.7753	Intermediate Similarity	NPC209318
0.7745	Intermediate Similarity	NPC86852
0.7745	Intermediate Similarity	NPC176949
0.7745	Intermediate Similarity	NPC251824
0.7745	Intermediate Similarity	NPC201908
0.7732	Intermediate Similarity	NPC223169
0.7732	Intermediate Similarity	NPC329910
0.7727	Intermediate Similarity	NPC47808
0.7727	Intermediate Similarity	NPC305835
0.7723	Intermediate Similarity	NPC84928
0.7723	Intermediate Similarity	NPC47281
0.7723	Intermediate Similarity	NPC98603
0.7717	Intermediate Similarity	NPC2783
0.7708	Intermediate Similarity	NPC470385
0.7708	Intermediate Similarity	NPC470386
0.7708	Intermediate Similarity	NPC272635
0.7708	Intermediate Similarity	NPC169751
0.7708	Intermediate Similarity	NPC100257
0.7708	Intermediate Similarity	NPC224410
0.7708	Intermediate Similarity	NPC47853
0.7701	Intermediate Similarity	NPC475932
0.7692	Intermediate Similarity	NPC474233
0.7692	Intermediate Similarity	NPC97505
0.7692	Intermediate Similarity	NPC139566
0.7692	Intermediate Similarity	NPC100391
0.7692	Intermediate Similarity	NPC475745
0.7692	Intermediate Similarity	NPC474482
0.7692	Intermediate Similarity	NPC219011
0.7684	Intermediate Similarity	NPC471901
0.7684	Intermediate Similarity	NPC475416
0.7684	Intermediate Similarity	NPC198242
0.7684	Intermediate Similarity	NPC211403
0.7677	Intermediate Similarity	NPC267921
0.7677	Intermediate Similarity	NPC287676
0.7677	Intermediate Similarity	NPC293866
0.7653	Intermediate Similarity	NPC96839
0.7653	Intermediate Similarity	NPC292133
0.7653	Intermediate Similarity	NPC253586
0.7647	Intermediate Similarity	NPC475571
0.7647	Intermediate Similarity	NPC28791
0.764	Intermediate Similarity	NPC206735
0.764	Intermediate Similarity	NPC304194
0.7634	Intermediate Similarity	NPC472497
0.7634	Intermediate Similarity	NPC174619
0.7634	Intermediate Similarity	NPC175293
0.7634	Intermediate Similarity	NPC264005
0.7634	Intermediate Similarity	NPC269360
0.7634	Intermediate Similarity	NPC153604
0.7634	Intermediate Similarity	NPC472495
0.7629	Intermediate Similarity	NPC280877
0.7624	Intermediate Similarity	NPC33973
0.7624	Intermediate Similarity	NPC36321
0.7624	Intermediate Similarity	NPC70967
0.7624	Intermediate Similarity	NPC266
0.7604	Intermediate Similarity	NPC474436
0.7604	Intermediate Similarity	NPC287118
0.7604	Intermediate Similarity	NPC63118
0.7604	Intermediate Similarity	NPC471902
0.7604	Intermediate Similarity	NPC473690
0.7604	Intermediate Similarity	NPC49776
0.76	Intermediate Similarity	NPC121218
0.76	Intermediate Similarity	NPC477053
0.76	Intermediate Similarity	NPC477051
0.76	Intermediate Similarity	NPC289148
0.76	Intermediate Similarity	NPC52899
0.76	Intermediate Similarity	NPC477052
0.76	Intermediate Similarity	NPC46848
0.76	Intermediate Similarity	NPC163963
0.76	Intermediate Similarity	NPC252614
0.76	Intermediate Similarity	NPC124211
0.76	Intermediate Similarity	NPC253886
0.7582	Intermediate Similarity	NPC475726
0.7582	Intermediate Similarity	NPC291320
0.7582	Intermediate Similarity	NPC472743
0.7582	Intermediate Similarity	NPC194637
0.7582	Intermediate Similarity	NPC471036
0.7579	Intermediate Similarity	NPC46758
0.7579	Intermediate Similarity	NPC471896
0.7576	Intermediate Similarity	NPC16911
0.7576	Intermediate Similarity	NPC252295
0.7576	Intermediate Similarity	NPC78427
0.7573	Intermediate Similarity	NPC131665
0.7573	Intermediate Similarity	NPC255387
0.7556	Intermediate Similarity	NPC58631
0.7556	Intermediate Similarity	NPC328264
0.7556	Intermediate Similarity	NPC475665
0.7556	Intermediate Similarity	NPC232625
0.7553	Intermediate Similarity	NPC16377
0.7553	Intermediate Similarity	NPC471900
0.7553	Intermediate Similarity	NPC146937
0.7551	Intermediate Similarity	NPC165616
0.7551	Intermediate Similarity	NPC307164
0.7551	Intermediate Similarity	NPC219353
0.7551	Intermediate Similarity	NPC256227
0.7549	Intermediate Similarity	NPC474558
0.7549	Intermediate Similarity	NPC469629
0.7549	Intermediate Similarity	NPC216245
0.7549	Intermediate Similarity	NPC470251
0.7549	Intermediate Similarity	NPC135854
0.7549	Intermediate Similarity	NPC29705
0.7549	Intermediate Similarity	NPC2436
0.7547	Intermediate Similarity	NPC40608
0.7527	Intermediate Similarity	NPC9892
0.7527	Intermediate Similarity	NPC91525
0.7527	Intermediate Similarity	NPC472505
0.7527	Intermediate Similarity	NPC10005
0.7527	Intermediate Similarity	NPC472738
0.7527	Intermediate Similarity	NPC264127
0.7527	Intermediate Similarity	NPC329943
0.7526	Intermediate Similarity	NPC159410
0.7526	Intermediate Similarity	NPC84893
0.7525	Intermediate Similarity	NPC170615
0.7525	Intermediate Similarity	NPC76866
0.7525	Intermediate Similarity	NPC275990
0.7525	Intermediate Similarity	NPC214946
0.7525	Intermediate Similarity	NPC246736
0.7525	Intermediate Similarity	NPC477054
0.7525	Intermediate Similarity	NPC286519
0.7525	Intermediate Similarity	NPC88203
0.7525	Intermediate Similarity	NPC124544
0.7525	Intermediate Similarity	NPC148628
0.7525	Intermediate Similarity	NPC53222
0.7525	Intermediate Similarity	NPC304832
0.75	Intermediate Similarity	NPC297265
0.75	Intermediate Similarity	NPC471035

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 NPC11611 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	2406
0.2-0.3	4229
0.3-0.4	1554
0.4-0.5	343
0.5-0.6	177
0.6-0.7	156
0.7-0.8	55
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
0.7872	Intermediate Similarity	NPD8034	Phase 2
0.7872	Intermediate Similarity	NPD8035	Phase 2
0.7802	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6672	Approved
0.7742	Intermediate Similarity	NPD5737	Approved
0.7576	Intermediate Similarity	NPD5696	Approved
0.7527	Intermediate Similarity	NPD6098	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.7476	Intermediate Similarity	NPD5739	Approved
0.7476	Intermediate Similarity	NPD6008	Approved
0.7476	Intermediate Similarity	NPD6675	Approved
0.7476	Intermediate Similarity	NPD6402	Approved
0.7476	Intermediate Similarity	NPD7128	Approved
0.7449	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6372	Approved
0.7429	Intermediate Similarity	NPD6373	Approved
0.7423	Intermediate Similarity	NPD6399	Phase 3
0.7404	Intermediate Similarity	NPD5701	Approved
0.7404	Intermediate Similarity	NPD5697	Approved
0.7368	Intermediate Similarity	NPD6903	Approved
0.7368	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7900	Approved
0.7347	Intermediate Similarity	NPD6001	Approved
0.7347	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7521	Approved
0.734	Intermediate Similarity	NPD6409	Approved
0.734	Intermediate Similarity	NPD6684	Approved
0.734	Intermediate Similarity	NPD5330	Approved
0.734	Intermediate Similarity	NPD7334	Approved
0.734	Intermediate Similarity	NPD7146	Approved
0.7333	Intermediate Similarity	NPD6881	Approved
0.7333	Intermediate Similarity	NPD6899	Approved
0.7333	Intermediate Similarity	NPD6011	Approved
0.7292	Intermediate Similarity	NPD6904	Approved
0.7292	Intermediate Similarity	NPD6080	Approved
0.7292	Intermediate Similarity	NPD6673	Approved
0.729	Intermediate Similarity	NPD6650	Approved
0.729	Intermediate Similarity	NPD6649	Approved
0.7264	Intermediate Similarity	NPD6012	Approved
0.7264	Intermediate Similarity	NPD6013	Approved
0.7264	Intermediate Similarity	NPD6014	Approved
0.72	Intermediate Similarity	NPD4697	Phase 3
0.7196	Intermediate Similarity	NPD7290	Approved
0.7196	Intermediate Similarity	NPD6883	Approved
0.7196	Intermediate Similarity	NPD7102	Approved
0.7172	Intermediate Similarity	NPD7748	Approved
0.7158	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD5693	Phase 1
0.713	Intermediate Similarity	NPD6869	Approved
0.713	Intermediate Similarity	NPD6617	Approved
0.713	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6847	Approved
0.713	Intermediate Similarity	NPD8130	Phase 1
0.7129	Intermediate Similarity	NPD7902	Approved
0.7129	Intermediate Similarity	NPD6084	Phase 2
0.7129	Intermediate Similarity	NPD6083	Phase 2
0.7126	Intermediate Similarity	NPD5777	Approved
0.7113	Intermediate Similarity	NPD5328	Approved
0.71	Intermediate Similarity	NPD5695	Phase 3
0.7083	Intermediate Similarity	NPD3573	Approved
0.7064	Intermediate Similarity	NPD6882	Approved
0.7064	Intermediate Similarity	NPD8297	Approved
0.7041	Intermediate Similarity	NPD5207	Approved
0.7041	Intermediate Similarity	NPD5692	Phase 3
0.703	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5221	Approved
0.703	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD6117	Approved
0.697	Remote Similarity	NPD5694	Approved
0.697	Remote Similarity	NPD6079	Approved
0.697	Remote Similarity	NPD6050	Approved
0.697	Remote Similarity	NPD7515	Phase 2
0.6966	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4755	Approved
0.6961	Remote Similarity	NPD5173	Approved
0.6947	Remote Similarity	NPD4786	Approved
0.6923	Remote Similarity	NPD6116	Phase 1
0.6915	Remote Similarity	NPD3667	Approved
0.6875	Remote Similarity	NPD6274	Approved
0.6875	Remote Similarity	NPD1694	Approved
0.6875	Remote Similarity	NPD6868	Approved
0.687	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6114	Approved
0.6848	Remote Similarity	NPD6697	Approved
0.6848	Remote Similarity	NPD6118	Approved
0.6848	Remote Similarity	NPD6115	Approved
0.6842	Remote Similarity	NPD4788	Approved
0.6837	Remote Similarity	NPD5208	Approved
0.6827	Remote Similarity	NPD4696	Approved
0.6827	Remote Similarity	NPD5285	Approved
0.6827	Remote Similarity	NPD4700	Approved
0.6827	Remote Similarity	NPD5286	Approved
0.6814	Remote Similarity	NPD6317	Approved
0.6771	Remote Similarity	NPD3668	Phase 3
0.6765	Remote Similarity	NPD4629	Approved
0.6765	Remote Similarity	NPD5210	Approved
0.6762	Remote Similarity	NPD5223	Approved
0.6759	Remote Similarity	NPD6614	Approved
0.6754	Remote Similarity	NPD6314	Approved
0.6754	Remote Similarity	NPD6335	Approved
0.6754	Remote Similarity	NPD6313	Approved
0.6744	Remote Similarity	NPD4224	Phase 2
0.6742	Remote Similarity	NPD6081	Approved
0.6742	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4202	Approved
0.6731	Remote Similarity	NPD7638	Approved
0.6705	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3702	Approved
0.6703	Remote Similarity	NPD3703	Phase 2
0.6698	Remote Similarity	NPD5225	Approved
0.6698	Remote Similarity	NPD5226	Approved
0.6698	Remote Similarity	NPD5211	Phase 2
0.6698	Remote Similarity	NPD4633	Approved
0.6698	Remote Similarity	NPD5224	Approved
0.6696	Remote Similarity	NPD4632	Approved
0.6696	Remote Similarity	NPD7100	Approved
0.6696	Remote Similarity	NPD7101	Approved
0.6695	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6639	Remote Similarity	NPD6616	Approved
0.6638	Remote Similarity	NPD6059	Approved
0.6638	Remote Similarity	NPD6319	Approved
0.6638	Remote Similarity	NPD6054	Approved
0.6636	Remote Similarity	NPD4754	Approved
0.6636	Remote Similarity	NPD5174	Approved
0.6636	Remote Similarity	NPD5175	Approved
0.6633	Remote Similarity	NPD5279	Phase 3
0.6629	Remote Similarity	NPD4789	Approved
0.6602	Remote Similarity	NPD5654	Approved
0.66	Remote Similarity	NPD4753	Phase 2
0.6598	Remote Similarity	NPD4197	Approved
0.6598	Remote Similarity	NPD3666	Approved
0.6598	Remote Similarity	NPD3665	Phase 1
0.6598	Remote Similarity	NPD3133	Approved
0.6583	Remote Similarity	NPD7078	Approved
0.6583	Remote Similarity	NPD8293	Discontinued
0.6581	Remote Similarity	NPD6908	Approved
0.6581	Remote Similarity	NPD5983	Phase 2
0.6581	Remote Similarity	NPD6016	Approved
0.6581	Remote Similarity	NPD6015	Approved
0.6581	Remote Similarity	NPD6909	Approved
0.6574	Remote Similarity	NPD5141	Approved
0.6562	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5329	Approved
0.6525	Remote Similarity	NPD6370	Approved
0.6525	Remote Similarity	NPD5988	Approved
0.6514	Remote Similarity	NPD4768	Approved
0.6514	Remote Similarity	NPD4767	Approved
0.6489	Remote Similarity	NPD3617	Approved
0.6481	Remote Similarity	NPD6052	Approved
0.6476	Remote Similarity	NPD5959	Approved
0.6471	Remote Similarity	NPD7604	Phase 2
0.6404	Remote Similarity	NPD5360	Phase 3
0.6404	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4729	Approved
0.6396	Remote Similarity	NPD5128	Approved
0.6396	Remote Similarity	NPD5168	Approved
0.6396	Remote Similarity	NPD4730	Approved
0.6392	Remote Similarity	NPD4223	Phase 3
0.6392	Remote Similarity	NPD4221	Approved
0.6381	Remote Similarity	NPD7732	Phase 3
0.6379	Remote Similarity	NPD7115	Discovery
0.6364	Remote Similarity	NPD6336	Discontinued
0.6354	Remote Similarity	NPD7525	Registered
0.6333	Remote Similarity	NPD3698	Phase 2
0.6333	Remote Similarity	NPD8328	Phase 3
0.6311	Remote Similarity	NPD5284	Approved
0.6311	Remote Similarity	NPD5281	Approved
0.63	Remote Similarity	NPD5280	Approved
0.63	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4694	Approved
0.63	Remote Similarity	NPD5690	Phase 2
0.6283	Remote Similarity	NPD5135	Approved
0.6283	Remote Similarity	NPD5247	Approved
0.6283	Remote Similarity	NPD5249	Phase 3
0.6283	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4634	Approved
0.6283	Remote Similarity	NPD5169	Approved
0.6283	Remote Similarity	NPD5251	Approved
0.6283	Remote Similarity	NPD5250	Approved
0.6283	Remote Similarity	NPD5248	Approved
0.6275	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6051	Approved
0.6264	Remote Similarity	NPD4244	Approved
0.6264	Remote Similarity	NPD4245	Approved
0.6264	Remote Similarity	NPD4747	Approved
0.6262	Remote Similarity	NPD4225	Approved
0.6261	Remote Similarity	NPD8133	Approved
0.626	Remote Similarity	NPD6033	Approved
0.625	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7632	Discontinued
0.6239	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5127	Approved
0.6228	Remote Similarity	NPD5217	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