NPASS Compound

Structure

CID15413 OpenBabel06191715342D 26 28 0 0 1 0 0 0 0 0999 V2000 1.8370 -3.7992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9297 0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2560 -3.1923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9002 -1.0288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6923 -2.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5068 -2.5457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1336 -1.9402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2410 -1.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2371 -2.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0342 -0.5288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6978 -2.1115 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4769 -1.5461 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2946 -0.9705 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3806 -2.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0800 -2.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2910 -1.1979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3232 -0.9463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5738 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9999 -0.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8330 -1.6054 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4342 -2.2749 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2732 -3.2445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5201 -3.9025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8207 -4.2372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5997 0.7852 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 9 2 0 0 0 0 2 10 2 0 0 0 0 3 6 1 0 0 0 0 3 9 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 7 15 1 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 11 5 1 1 0 0 0 11 16 1 0 0 0 0 12 6 1 1 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 8 1 6 0 0 0 13 19 1 0 0 0 0 14 7 1 6 0 0 0 14 18 1 0 0 0 0 14 21 1 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 16 10 1 1 0 0 0 16 17 1 0 0 0 0 17 26 1 6 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 25 2 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.18
Volume:	364.273
LogP:	-0.444
LogD:	0.779
LogS:	-2.132
# Rotatable Bonds:	6
TPSA:	118.72
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	4.493
Fsp3:	0.632
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.901
MDCK Permeability:	4.1411705751670524e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.065
20% Bioavailability (F20%):	0.929
30% Bioavailability (F30%):	0.207

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.581
Plasma Protein Binding (PPB):	48.931846618652344%
Volume Distribution (VD):	0.394
Pgp-substrate:	67.14459991455078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.036
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	4.517
Half-life (T1/2):	0.613

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.822
Drug-inuced Liver Injury (DILI):	0.155
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.372
Maximum Recommended Daily Dose:	0.768
Skin Sensitization:	0.103
Carcinogencity:	0.48
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.331

Download Data

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

Natural Product: NPC15413

Natural Product ID:	NPC15413
*Common Name:**	Saussureamine C
IUPAC Name:	(2S)-2-[[(3R,3aS,6aR,9aR,9bS)-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-3-yl]methylamino]-4-amino-4-oxobutanoic acid
Synonyms:
Standard InCHIKey:	MZFVEYVQALPRDY-HHHJXDIYSA-N
Standard InCHI:	InChI=1S/C19H26N2O5/c1-9-3-6-12-13(8-21-14(18(23)24)7-15(20)22)19(25)26-17(12)16-10(2)4-5-11(9)16/h11-14,16-17,21H,1-8H2,(H2,20,22)(H,23,24)/t11-,12-,13-,14-,16-,17-/m0/s1
SMILES:	C=C1CC[C@H]2[C@H](CN[C@@H](CC(=N)O)C(=O)O)C(=O)O[C@@H]2[C@H]2C(=C)CC[C@@H]12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3220830
PubChem CID:	9998735
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:0001770] Guaianolides 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
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[14510592]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25825	Saussurea lappa	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	1
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	4.7	%	PMID[481400]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	68.1	%	PMID[481400]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16.0	ug.mL-1	PMID[481400]

☑ 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 NPC15413 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	96
0.1-0.2	911
0.2-0.3	15226
0.3-0.4	16231
0.4-0.5	8768
0.5-0.6	1342
0.6-0.7	114
0.7-0.8	3
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9252	High Similarity	NPC209734
0.8704	High Similarity	NPC76660
0.8704	High Similarity	NPC276995
0.8302	Intermediate Similarity	NPC265094
0.8148	Intermediate Similarity	NPC236644
0.8036	Intermediate Similarity	NPC469466
0.712	Intermediate Similarity	NPC474371
0.6983	Remote Similarity	NPC271562
0.6912	Remote Similarity	NPC57976
0.661	Remote Similarity	NPC233256
0.661	Remote Similarity	NPC195841
0.65	Remote Similarity	NPC70235
0.6481	Remote Similarity	NPC90476
0.6481	Remote Similarity	NPC69374
0.6476	Remote Similarity	NPC51507
0.6435	Remote Similarity	NPC476344
0.6404	Remote Similarity	NPC150041
0.6387	Remote Similarity	NPC119329
0.6378	Remote Similarity	NPC35037
0.6364	Remote Similarity	NPC171734
0.6341	Remote Similarity	NPC79238
0.6325	Remote Similarity	NPC239768
0.6325	Remote Similarity	NPC128698
0.6306	Remote Similarity	NPC203170
0.6303	Remote Similarity	NPC215988
0.63	Remote Similarity	NPC5714
0.6296	Remote Similarity	NPC128246
0.6296	Remote Similarity	NPC111409
0.6288	Remote Similarity	NPC317654
0.6288	Remote Similarity	NPC96010
0.6262	Remote Similarity	NPC126248
0.6261	Remote Similarity	NPC40663
0.625	Remote Similarity	NPC477237
0.6241	Remote Similarity	NPC478136
0.6218	Remote Similarity	NPC471258
0.6218	Remote Similarity	NPC475149
0.6218	Remote Similarity	NPC471097
0.6207	Remote Similarity	NPC476449
0.6168	Remote Similarity	NPC156658
0.6168	Remote Similarity	NPC258965
0.6161	Remote Similarity	NPC322966
0.6161	Remote Similarity	NPC207114
0.6161	Remote Similarity	NPC217983
0.6154	Remote Similarity	NPC477238
0.6126	Remote Similarity	NPC187661
0.6126	Remote Similarity	NPC236692
0.6126	Remote Similarity	NPC309757
0.6124	Remote Similarity	NPC471261
0.6106	Remote Similarity	NPC477729
0.6106	Remote Similarity	NPC38392
0.6091	Remote Similarity	NPC224386
0.6091	Remote Similarity	NPC227051
0.6091	Remote Similarity	NPC194859
0.608	Remote Similarity	NPC476875
0.608	Remote Similarity	NPC474459
0.6077	Remote Similarity	NPC11379
0.6071	Remote Similarity	NPC118601
0.6066	Remote Similarity	NPC241394
0.6066	Remote Similarity	NPC471259
0.6063	Remote Similarity	NPC471645
0.6058	Remote Similarity	NPC133089
0.6058	Remote Similarity	NPC320537
0.6058	Remote Similarity	NPC143979
0.6055	Remote Similarity	NPC246076
0.6053	Remote Similarity	NPC54065
0.6053	Remote Similarity	NPC19087
0.6053	Remote Similarity	NPC297474
0.605	Remote Similarity	NPC13175
0.605	Remote Similarity	NPC475791
0.6047	Remote Similarity	NPC476952
0.6047	Remote Similarity	NPC174463
0.6032	Remote Similarity	NPC474452
0.6031	Remote Similarity	NPC23963
0.6029	Remote Similarity	NPC478139
0.6018	Remote Similarity	NPC178875
0.6018	Remote Similarity	NPC53158
0.6018	Remote Similarity	NPC79549
0.6	Remote Similarity	NPC54468
0.6	Remote Similarity	NPC171360
0.6	Remote Similarity	NPC29821
0.6	Remote Similarity	NPC95478
0.6	Remote Similarity	NPC133888
0.6	Remote Similarity	NPC35959
0.6	Remote Similarity	NPC145748
0.6	Remote Similarity	NPC155670
0.6	Remote Similarity	NPC184063
0.6	Remote Similarity	NPC475925
0.6	Remote Similarity	NPC245665
0.6	Remote Similarity	NPC472313
0.6	Remote Similarity	NPC57304
0.6	Remote Similarity	NPC63193
0.6	Remote Similarity	NPC293001
0.5984	Remote Similarity	NPC128303
0.5984	Remote Similarity	NPC14537
0.5984	Remote Similarity	NPC106479
0.5984	Remote Similarity	NPC469597
0.597	Remote Similarity	NPC309525
0.5966	Remote Similarity	NPC234542
0.5966	Remote Similarity	NPC220234
0.5966	Remote Similarity	NPC475758
0.5965	Remote Similarity	NPC12872
0.5965	Remote Similarity	NPC215556
0.5965	Remote Similarity	NPC155935
0.5965	Remote Similarity	NPC168679
0.5954	Remote Similarity	NPC88190
0.5954	Remote Similarity	NPC139867
0.5954	Remote Similarity	NPC230849
0.5952	Remote Similarity	NPC66862
0.5952	Remote Similarity	NPC147238
0.5952	Remote Similarity	NPC58281
0.5948	Remote Similarity	NPC475788
0.5946	Remote Similarity	NPC165287
0.5938	Remote Similarity	NPC470540
0.5935	Remote Similarity	NPC471844
0.5935	Remote Similarity	NPC86906
0.5935	Remote Similarity	NPC473252
0.5932	Remote Similarity	NPC471843
0.5929	Remote Similarity	NPC201658
0.5929	Remote Similarity	NPC304454
0.5926	Remote Similarity	NPC476951
0.5926	Remote Similarity	NPC216090
0.5923	Remote Similarity	NPC470276
0.5917	Remote Similarity	NPC473224
0.5913	Remote Similarity	NPC35809
0.5913	Remote Similarity	NPC216284
0.5909	Remote Similarity	NPC315188
0.5906	Remote Similarity	NPC124358
0.5902	Remote Similarity	NPC471260
0.5893	Remote Similarity	NPC204105
0.5893	Remote Similarity	NPC284534
0.5893	Remote Similarity	NPC300082
0.5891	Remote Similarity	NPC28280
0.5891	Remote Similarity	NPC304646
0.589	Remote Similarity	NPC477519
0.5888	Remote Similarity	NPC208223
0.5887	Remote Similarity	NPC244982
0.5887	Remote Similarity	NPC476756
0.5873	Remote Similarity	NPC63511
0.5873	Remote Similarity	NPC72753
0.5872	Remote Similarity	NPC314466
0.5868	Remote Similarity	NPC188785
0.5868	Remote Similarity	NPC474348
0.5865	Remote Similarity	NPC471262
0.5862	Remote Similarity	NPC142761
0.5862	Remote Similarity	NPC155215
0.5862	Remote Similarity	NPC133698
0.5859	Remote Similarity	NPC130124
0.5859	Remote Similarity	NPC193471
0.5854	Remote Similarity	NPC477001
0.5854	Remote Similarity	NPC64168
0.5854	Remote Similarity	NPC74035
0.5854	Remote Similarity	NPC477000
0.5847	Remote Similarity	NPC163228
0.5847	Remote Similarity	NPC472873
0.5847	Remote Similarity	NPC476053
0.5846	Remote Similarity	NPC201968
0.5846	Remote Similarity	NPC147707
0.5842	Remote Similarity	NPC470109
0.5841	Remote Similarity	NPC56593
0.5841	Remote Similarity	NPC238593
0.5841	Remote Similarity	NPC304558
0.5841	Remote Similarity	NPC64153
0.5839	Remote Similarity	NPC470539
0.5827	Remote Similarity	NPC474411
0.5827	Remote Similarity	NPC30911
0.5827	Remote Similarity	NPC474431
0.5827	Remote Similarity	NPC316984
0.5826	Remote Similarity	NPC159369
0.5826	Remote Similarity	NPC39290
0.5818	Remote Similarity	NPC255580
0.5818	Remote Similarity	NPC39411
0.5814	Remote Similarity	NPC50694
0.5812	Remote Similarity	NPC60386
0.5812	Remote Similarity	NPC308656
0.5812	Remote Similarity	NPC473273
0.5812	Remote Similarity	NPC258216
0.5812	Remote Similarity	NPC473234
0.5812	Remote Similarity	NPC469998
0.5812	Remote Similarity	NPC153590
0.5812	Remote Similarity	NPC473263
0.581	Remote Similarity	NPC43219
0.5804	Remote Similarity	NPC156485
0.5802	Remote Similarity	NPC9714
0.5802	Remote Similarity	NPC471109
0.5802	Remote Similarity	NPC235625
0.5798	Remote Similarity	NPC91771
0.5798	Remote Similarity	NPC142529
0.5798	Remote Similarity	NPC160066
0.5798	Remote Similarity	NPC474297
0.5798	Remote Similarity	NPC24956
0.5798	Remote Similarity	NPC18019
0.5797	Remote Similarity	NPC307165
0.5789	Remote Similarity	NPC24728
0.5789	Remote Similarity	NPC237540
0.5789	Remote Similarity	NPC475773
0.5789	Remote Similarity	NPC160688
0.5784	Remote Similarity	NPC470110
0.5776	Remote Similarity	NPC47230
0.5776	Remote Similarity	NPC17143
0.5772	Remote Similarity	NPC173690

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 NPC15413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	78
0.1-0.2	546
0.2-0.3	3563
0.3-0.4	3788
0.4-0.5	971
0.5-0.6	201
0.6-0.7	3
0.7-0.8	0
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
0.6667	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD617	Approved
0.6393	Remote Similarity	NPD6420	Discontinued
0.6283	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD8175	Discontinued
0.6099	Remote Similarity	NPD6852	Discontinued
0.6031	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD7751	Phase 1
0.6017	Remote Similarity	NPD3715	Approved
0.6017	Remote Similarity	NPD3714	Approved
0.6017	Remote Similarity	NPD3713	Approved
0.6	Remote Similarity	NPD7517	Approved
0.6	Remote Similarity	NPD7518	Approved
0.6	Remote Similarity	NPD7519	Approved
0.5954	Remote Similarity	NPD1689	Approved
0.5944	Remote Similarity	NPD6077	Discontinued
0.5932	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.59	Remote Similarity	NPD9201	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD573	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD6421	Discontinued
0.5865	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7623	Phase 3
0.5859	Remote Similarity	NPD8298	Phase 2
0.5859	Remote Similarity	NPD1376	Discontinued
0.5841	Remote Similarity	NPD3176	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7147	Phase 3
0.5827	Remote Similarity	NPD2204	Approved
0.5789	Remote Similarity	NPD621	Discontinued
0.5776	Remote Similarity	NPD2682	Approved
0.5772	Remote Similarity	NPD2259	Approved
0.5772	Remote Similarity	NPD2258	Approved
0.576	Remote Similarity	NPD1827	Clinical (unspecified phase)
0.576	Remote Similarity	NPD1828	Approved
0.576	Remote Similarity	NPD1829	Clinical (unspecified phase)
0.576	Remote Similarity	NPD1126	Phase 2
0.5758	Remote Similarity	NPD2132	Phase 3
0.5755	Remote Similarity	NPD2101	Approved
0.5726	Remote Similarity	NPD1749	Approved
0.5725	Remote Similarity	NPD1348	Approved
0.5714	Remote Similarity	NPD2256	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.5704	Remote Similarity	NPD7122	Discontinued
0.5694	Remote Similarity	NPD5725	Approved
0.5693	Remote Similarity	NPD7746	Phase 1
0.5693	Remote Similarity	NPD7747	Phase 1
0.5676	Remote Similarity	NPD857	Phase 3
0.5672	Remote Similarity	NPD8267	Approved
0.5672	Remote Similarity	NPD8269	Approved
0.5672	Remote Similarity	NPD8268	Approved
0.5672	Remote Similarity	NPD8266	Approved
0.5669	Remote Similarity	NPD6413	Approved
0.5664	Remote Similarity	NPD4153	Approved
0.5664	Remote Similarity	NPD8416	Discontinued
0.5659	Remote Similarity	NPD7336	Phase 2
0.5659	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD7335	Phase 2
0.5643	Remote Similarity	NPD4175	Approved
0.5643	Remote Similarity	NPD4177	Approved
0.5641	Remote Similarity	NPD4261	Phase 1
0.5625	Remote Similarity	NPD8087	Discontinued
0.562	Remote Similarity	NPD3677	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.56	Remote Similarity	NPD9676	Phase 3

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