NPASS Compound

Structure

NPC476292 OpenBabel07101718282D 28 30 0 0 1 0 0 0 0 0999 V2000 -6.9300 -1.1248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5999 0.3752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8966 -3.3461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5832 0.6651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0640 -0.6248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9659 -1.9909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1980 -3.1248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0640 -2.6248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3320 -2.6248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3320 0.3752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5176 -1.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 -1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1980 -0.1248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4659 -1.1248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0640 -1.6248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4659 -0.1248 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1554 -2.3801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4483 -1.6730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3320 -1.6248 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1213 -2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 -0.2588 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1980 -1.1248 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4659 -1.1248 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8284 -2.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3801 -1.1554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -0.7071 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 16 2 0 0 0 0 2 17 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 16 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 24 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 1 0 0 0 18 3 1 6 0 0 0 18 21 1 0 0 0 0 19 18 1 1 0 0 0 19 27 1 0 0 0 0 20 23 1 1 0 0 0 20 24 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 22 4 1 6 0 0 0 22 28 1 0 0 0 0 23 5 1 1 0 0 0 24 6 1 1 0 0 0 27 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.29
Volume:	427.879
LogP:	4.437
LogD:	3.465
LogS:	-4.809
# Rotatable Bonds:	5
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.45
Synthetic Accessibility Score:	4.929
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.181
MDCK Permeability:	2.239593413833063e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097
Plasma Protein Binding (PPB):	96.32671356201172%
Volume Distribution (VD):	0.962
Pgp-substrate:	2.7653815746307373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.733
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.722
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.808
CYP3A4-inhibitor:	0.163
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	2.753
Half-life (T1/2):	0.523

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.405
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.735
Carcinogencity:	0.067
Eye Corrosion:	0.331
Eye Irritation:	0.569
Respiratory Toxicity:	0.813

Download Data

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

Natural Product: NPC476292

Natural Product ID:	NPC476292
*Common Name:**	(+)-Sigmosceptrellin A
IUPAC Name:	(2R)-2-[(3R,6R)-6-[2-[(1S,2R,4aR,8aR)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]ethyl]-6-methyldioxan-3-yl]propanoic acid
Synonyms:	(+)-Sigmosceptrellin A
Standard InCHIKey:	SQNNYRWDFNZPBJ-UNTXESCWSA-N
Standard InCHI:	InChI=1S/C24H40O4/c1-16-8-7-9-20-23(16,5)13-10-17(2)24(20,6)15-14-22(4)12-11-19(27-28-22)18(3)21(25)26/h17-20H,1,7-15H2,2-6H3,(H,25,26)/t17-,18-,19-,20+,22+,23+,24+/m1/s1
SMILES:	C[C@H]([C@H]1CC[C@@](OO1)(C)CC[C@@]1(C)[C@H](C)CC[C@@]2([C@@H]1CCCC2=C)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562438
PubChem CID:	45267058
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO4185	Diacarnus bismarckensis	Species	Podospongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159277]

☑ 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

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	1.0	ug.mL-1	PMID[496403]

☑ 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 NPC476292 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	195
0.1-0.2	1628
0.2-0.3	6276
0.3-0.4	15236
0.4-0.5	6991
0.5-0.6	6396
0.6-0.7	4576
0.7-0.8	1303
0.8-0.85	78
0.85-0.9	8
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474605
0.9481	High Similarity	NPC274522
0.9481	High Similarity	NPC476265
0.9474	High Similarity	NPC470905
0.9474	High Similarity	NPC476986
0.9259	High Similarity	NPC262085
0.9125	High Similarity	NPC476100
0.9	High Similarity	NPC475395
0.9	High Similarity	NPC476984
0.8961	High Similarity	NPC475744
0.8961	High Similarity	NPC476985
0.8961	High Similarity	NPC474316
0.8846	High Similarity	NPC469867
0.8795	High Similarity	NPC475181
0.8675	High Similarity	NPC471344
0.8642	High Similarity	NPC117960
0.8642	High Similarity	NPC14044
0.8642	High Similarity	NPC172309
0.8571	High Similarity	NPC476104
0.8488	Intermediate Similarity	NPC471342
0.8488	Intermediate Similarity	NPC469866
0.8471	Intermediate Similarity	NPC134197
0.8434	Intermediate Similarity	NPC476983
0.8415	Intermediate Similarity	NPC476988
0.8395	Intermediate Similarity	NPC308545
0.8395	Intermediate Similarity	NPC82488
0.8375	Intermediate Similarity	NPC474433
0.8372	Intermediate Similarity	NPC255176
0.8372	Intermediate Similarity	NPC183374
0.8372	Intermediate Similarity	NPC211162
0.8333	Intermediate Similarity	NPC120158
0.8333	Intermediate Similarity	NPC475193
0.8312	Intermediate Similarity	NPC91369
0.8289	Intermediate Similarity	NPC290445
0.8289	Intermediate Similarity	NPC36616
0.8276	Intermediate Similarity	NPC57954
0.8276	Intermediate Similarity	NPC213832
0.8235	Intermediate Similarity	NPC201655
0.8214	Intermediate Similarity	NPC471037
0.8205	Intermediate Similarity	NPC72343
0.8161	Intermediate Similarity	NPC471900
0.8161	Intermediate Similarity	NPC56413
0.8161	Intermediate Similarity	NPC146937
0.8148	Intermediate Similarity	NPC122847
0.8148	Intermediate Similarity	NPC66105
0.814	Intermediate Similarity	NPC476982
0.814	Intermediate Similarity	NPC80590
0.814	Intermediate Similarity	NPC73038
0.8132	Intermediate Similarity	NPC132824
0.8101	Intermediate Similarity	NPC36310
0.809	Intermediate Similarity	NPC288833
0.809	Intermediate Similarity	NPC966
0.809	Intermediate Similarity	NPC228784
0.809	Intermediate Similarity	NPC471588
0.809	Intermediate Similarity	NPC471901
0.809	Intermediate Similarity	NPC324341
0.809	Intermediate Similarity	NPC155120
0.809	Intermediate Similarity	NPC282616
0.809	Intermediate Similarity	NPC6255
0.8072	Intermediate Similarity	NPC37038
0.8068	Intermediate Similarity	NPC77001
0.8068	Intermediate Similarity	NPC24772
0.8068	Intermediate Similarity	NPC116146
0.8068	Intermediate Similarity	NPC253618
0.8049	Intermediate Similarity	NPC321514
0.8049	Intermediate Similarity	NPC476810
0.8046	Intermediate Similarity	NPC158141
0.8046	Intermediate Similarity	NPC96496
0.8046	Intermediate Similarity	NPC269360
0.8046	Intermediate Similarity	NPC173089
0.8046	Intermediate Similarity	NPC264005
0.8043	Intermediate Similarity	NPC253586
0.8025	Intermediate Similarity	NPC469514
0.8025	Intermediate Similarity	NPC476987
0.8025	Intermediate Similarity	NPC59602
0.8025	Intermediate Similarity	NPC246445
0.8025	Intermediate Similarity	NPC152754
0.8023	Intermediate Similarity	NPC76333
0.8022	Intermediate Similarity	NPC205173
0.8	Intermediate Similarity	NPC199543
0.8	Intermediate Similarity	NPC46610
0.8	Intermediate Similarity	NPC18819
0.8	Intermediate Similarity	NPC473690
0.8	Intermediate Similarity	NPC471902
0.8	Intermediate Similarity	NPC243347
0.8	Intermediate Similarity	NPC245866
0.8	Intermediate Similarity	NPC118490
0.8	Intermediate Similarity	NPC287118
0.7978	Intermediate Similarity	NPC130278
0.7978	Intermediate Similarity	NPC172361
0.7978	Intermediate Similarity	NPC169933
0.7978	Intermediate Similarity	NPC86372
0.7976	Intermediate Similarity	NPC475951
0.7976	Intermediate Similarity	NPC327002
0.7957	Intermediate Similarity	NPC474793
0.7957	Intermediate Similarity	NPC174663
0.7955	Intermediate Similarity	NPC1753
0.7955	Intermediate Similarity	NPC474511
0.7952	Intermediate Similarity	NPC231431
0.7935	Intermediate Similarity	NPC201657
0.7931	Intermediate Similarity	NPC475007
0.7931	Intermediate Similarity	NPC322159
0.7931	Intermediate Similarity	NPC472505
0.7931	Intermediate Similarity	NPC187545
0.7931	Intermediate Similarity	NPC2783
0.7931	Intermediate Similarity	NPC324063
0.7931	Intermediate Similarity	NPC70661
0.7927	Intermediate Similarity	NPC476325
0.7927	Intermediate Similarity	NPC476264
0.7927	Intermediate Similarity	NPC238227
0.7912	Intermediate Similarity	NPC191412
0.7912	Intermediate Similarity	NPC114159
0.7912	Intermediate Similarity	NPC78580
0.7912	Intermediate Similarity	NPC184006
0.7912	Intermediate Similarity	NPC23621
0.7912	Intermediate Similarity	NPC222047
0.7912	Intermediate Similarity	NPC6818
0.7912	Intermediate Similarity	NPC469982
0.7912	Intermediate Similarity	NPC148964
0.7907	Intermediate Similarity	NPC263974
0.7907	Intermediate Similarity	NPC471343
0.7889	Intermediate Similarity	NPC475416
0.7882	Intermediate Similarity	NPC170985
0.7882	Intermediate Similarity	NPC145143
0.7875	Intermediate Similarity	NPC161187
0.7875	Intermediate Similarity	NPC330659
0.7875	Intermediate Similarity	NPC244708
0.7872	Intermediate Similarity	NPC108371
0.7872	Intermediate Similarity	NPC35239
0.7865	Intermediate Similarity	NPC64872
0.7865	Intermediate Similarity	NPC225585
0.7865	Intermediate Similarity	NPC270768
0.7865	Intermediate Similarity	NPC25906
0.7865	Intermediate Similarity	NPC293048
0.7865	Intermediate Similarity	NPC59263
0.7865	Intermediate Similarity	NPC290972
0.7865	Intermediate Similarity	NPC61543
0.7865	Intermediate Similarity	NPC234346
0.7865	Intermediate Similarity	NPC127689
0.7865	Intermediate Similarity	NPC474700
0.7865	Intermediate Similarity	NPC474704
0.7865	Intermediate Similarity	NPC475921
0.7865	Intermediate Similarity	NPC130520
0.7865	Intermediate Similarity	NPC121798
0.7865	Intermediate Similarity	NPC263393
0.7865	Intermediate Similarity	NPC474570
0.7857	Intermediate Similarity	NPC104545
0.7849	Intermediate Similarity	NPC261935
0.7849	Intermediate Similarity	NPC187933
0.7849	Intermediate Similarity	NPC106112
0.7841	Intermediate Similarity	NPC477926
0.7841	Intermediate Similarity	NPC33768
0.7831	Intermediate Similarity	NPC110094
0.7831	Intermediate Similarity	NPC260385
0.7831	Intermediate Similarity	NPC269543
0.7831	Intermediate Similarity	NPC280654
0.7831	Intermediate Similarity	NPC321690
0.7831	Intermediate Similarity	NPC121200
0.7831	Intermediate Similarity	NPC247783
0.7826	Intermediate Similarity	NPC266431
0.7826	Intermediate Similarity	NPC23241
0.7826	Intermediate Similarity	NPC195715
0.7826	Intermediate Similarity	NPC263135
0.7826	Intermediate Similarity	NPC210214
0.7826	Intermediate Similarity	NPC148523
0.7826	Intermediate Similarity	NPC288906
0.7816	Intermediate Similarity	NPC264317
0.7816	Intermediate Similarity	NPC294438
0.7816	Intermediate Similarity	NPC329738
0.7805	Intermediate Similarity	NPC476601
0.7805	Intermediate Similarity	NPC89294
0.7805	Intermediate Similarity	NPC104806
0.7805	Intermediate Similarity	NPC20466
0.7802	Intermediate Similarity	NPC298554
0.7802	Intermediate Similarity	NPC202728
0.7802	Intermediate Similarity	NPC229281
0.7802	Intermediate Similarity	NPC158059
0.7802	Intermediate Similarity	NPC118519
0.7792	Intermediate Similarity	NPC103734
0.7791	Intermediate Similarity	NPC477373
0.7789	Intermediate Similarity	NPC236585
0.7778	Intermediate Similarity	NPC227467
0.7778	Intermediate Similarity	NPC193750
0.7778	Intermediate Similarity	NPC7260
0.7778	Intermediate Similarity	NPC120968
0.7778	Intermediate Similarity	NPC111110
0.7778	Intermediate Similarity	NPC273621
0.7778	Intermediate Similarity	NPC263977
0.7778	Intermediate Similarity	NPC126369
0.7778	Intermediate Similarity	NPC290614
0.7778	Intermediate Similarity	NPC210037
0.7778	Intermediate Similarity	NPC18872
0.7778	Intermediate Similarity	NPC255168
0.7778	Intermediate Similarity	NPC470589
0.7778	Intermediate Similarity	NPC477872
0.7766	Intermediate Similarity	NPC271614
0.7766	Intermediate Similarity	NPC164349
0.7766	Intermediate Similarity	NPC111214
0.7766	Intermediate Similarity	NPC29765
0.7765	Intermediate Similarity	NPC232625

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 NPC476292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	2124
0.2-0.3	3901
0.3-0.4	1948
0.4-0.5	536
0.5-0.6	234
0.6-0.7	187
0.7-0.8	25
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
0.7816	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8034	Phase 2
0.7692	Intermediate Similarity	NPD8035	Phase 2
0.7609	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD6411	Approved
0.7386	Intermediate Similarity	NPD4788	Approved
0.734	Intermediate Similarity	NPD7748	Approved
0.7303	Intermediate Similarity	NPD4786	Approved
0.7294	Intermediate Similarity	NPD6116	Phase 1
0.7292	Intermediate Similarity	NPD6083	Phase 2
0.7292	Intermediate Similarity	NPD6084	Phase 2
0.7292	Intermediate Similarity	NPD7902	Approved
0.7283	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6101	Approved
0.7273	Intermediate Similarity	NPD3667	Approved
0.7176	Intermediate Similarity	NPD6117	Approved
0.7157	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.7129	Intermediate Similarity	NPD5739	Approved
0.7129	Intermediate Similarity	NPD6675	Approved
0.7129	Intermediate Similarity	NPD6402	Approved
0.7129	Intermediate Similarity	NPD7128	Approved
0.7111	Intermediate Similarity	NPD3133	Approved
0.7111	Intermediate Similarity	NPD3665	Phase 1
0.7111	Intermediate Similarity	NPD3666	Approved
0.7097	Intermediate Similarity	NPD4753	Phase 2
0.7083	Intermediate Similarity	NPD5695	Phase 3
0.7059	Intermediate Similarity	NPD3702	Approved
0.7041	Intermediate Similarity	NPD5696	Approved
0.7011	Intermediate Similarity	NPD6114	Approved
0.7011	Intermediate Similarity	NPD6697	Approved
0.7011	Intermediate Similarity	NPD6115	Approved
0.7011	Intermediate Similarity	NPD6118	Approved
0.699	Remote Similarity	NPD6881	Approved
0.699	Remote Similarity	NPD7320	Approved
0.699	Remote Similarity	NPD6899	Approved
0.6989	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5737	Approved
0.6989	Remote Similarity	NPD6672	Approved
0.6989	Remote Similarity	NPD6903	Approved
0.6979	Remote Similarity	NPD7900	Approved
0.6979	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3618	Phase 1
0.6947	Remote Similarity	NPD5281	Approved
0.6947	Remote Similarity	NPD5284	Approved
0.6939	Remote Similarity	NPD4755	Approved
0.6923	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD3668	Phase 3
0.6923	Remote Similarity	NPD6373	Approved
0.6915	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5328	Approved
0.6914	Remote Similarity	NPD4224	Phase 2
0.6905	Remote Similarity	NPD6081	Approved
0.6893	Remote Similarity	NPD5701	Approved
0.6893	Remote Similarity	NPD5697	Approved
0.6889	Remote Similarity	NPD4221	Approved
0.6889	Remote Similarity	NPD4223	Phase 3
0.6875	Remote Similarity	NPD4202	Approved
0.6857	Remote Similarity	NPD6883	Approved
0.6857	Remote Similarity	NPD7290	Approved
0.6857	Remote Similarity	NPD7102	Approved
0.6854	Remote Similarity	NPD7525	Registered
0.6854	Remote Similarity	NPD4695	Discontinued
0.6848	Remote Similarity	NPD5329	Approved
0.6827	Remote Similarity	NPD6686	Approved
0.6822	Remote Similarity	NPD8133	Approved
0.68	Remote Similarity	NPD5285	Approved
0.68	Remote Similarity	NPD4696	Approved
0.68	Remote Similarity	NPD5286	Approved
0.68	Remote Similarity	NPD4700	Approved
0.6792	Remote Similarity	NPD6847	Approved
0.6792	Remote Similarity	NPD6617	Approved
0.6792	Remote Similarity	NPD6650	Approved
0.6792	Remote Similarity	NPD6869	Approved
0.6792	Remote Similarity	NPD8130	Phase 1
0.6792	Remote Similarity	NPD6649	Approved
0.6786	Remote Similarity	NPD4244	Approved
0.6786	Remote Similarity	NPD4245	Approved
0.6774	Remote Similarity	NPD6098	Approved
0.6771	Remote Similarity	NPD6079	Approved
0.6762	Remote Similarity	NPD6013	Approved
0.6762	Remote Similarity	NPD6014	Approved
0.6762	Remote Similarity	NPD6012	Approved
0.6739	Remote Similarity	NPD4197	Approved
0.6737	Remote Similarity	NPD6904	Approved
0.6737	Remote Similarity	NPD6673	Approved
0.6737	Remote Similarity	NPD6080	Approved
0.6735	Remote Similarity	NPD5210	Approved
0.6735	Remote Similarity	NPD4629	Approved
0.6731	Remote Similarity	NPD6412	Phase 2
0.6729	Remote Similarity	NPD8297	Approved
0.6729	Remote Similarity	NPD6882	Approved
0.6706	Remote Similarity	NPD5777	Approved
0.6706	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3573	Approved
0.6701	Remote Similarity	NPD5779	Approved
0.6701	Remote Similarity	NPD5778	Approved
0.67	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD3698	Phase 2
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD7115	Discovery
0.6636	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7639	Approved
0.6634	Remote Similarity	NPD7640	Approved
0.6629	Remote Similarity	NPD3617	Approved
0.6604	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5175	Approved
0.6602	Remote Similarity	NPD5174	Approved
0.6598	Remote Similarity	NPD7637	Suspended
0.6596	Remote Similarity	NPD4623	Approved
0.6596	Remote Similarity	NPD4690	Approved
0.6596	Remote Similarity	NPD5279	Phase 3
0.6596	Remote Similarity	NPD4689	Approved
0.6596	Remote Similarity	NPD4688	Approved
0.6596	Remote Similarity	NPD4138	Approved
0.6596	Remote Similarity	NPD5205	Approved
0.6596	Remote Similarity	NPD4693	Phase 3
0.6596	Remote Similarity	NPD4519	Discontinued
0.6593	Remote Similarity	NPD5369	Approved
0.6588	Remote Similarity	NPD4789	Approved
0.6585	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5223	Approved
0.6566	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7645	Phase 2
0.6548	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5360	Phase 3
0.6542	Remote Similarity	NPD4634	Approved
0.6538	Remote Similarity	NPD5141	Approved
0.6535	Remote Similarity	NPD4225	Approved
0.65	Remote Similarity	NPD5221	Approved
0.65	Remote Similarity	NPD5222	Approved
0.65	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7614	Phase 1
0.65	Remote Similarity	NPD4697	Phase 3
0.6486	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5368	Approved
0.6477	Remote Similarity	NPD7339	Approved
0.6477	Remote Similarity	NPD6942	Approved
0.6476	Remote Similarity	NPD4767	Approved
0.6476	Remote Similarity	NPD4768	Approved
0.6465	Remote Similarity	NPD5282	Discontinued
0.646	Remote Similarity	NPD6319	Approved
0.6458	Remote Similarity	NPD5208	Approved
0.6449	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4754	Approved
0.6436	Remote Similarity	NPD5173	Approved
0.6435	Remote Similarity	NPD8328	Phase 3
0.6429	Remote Similarity	NPD6050	Approved
0.6429	Remote Similarity	NPD5693	Phase 1
0.6421	Remote Similarity	NPD5690	Phase 2
0.6421	Remote Similarity	NPD4694	Approved
0.6421	Remote Similarity	NPD5280	Approved
0.6413	Remote Similarity	NPD4692	Approved
0.6413	Remote Similarity	NPD4139	Approved
0.6404	Remote Similarity	NPD6921	Approved
0.6404	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6274	Approved
0.6392	Remote Similarity	NPD6051	Approved
0.6389	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7492	Approved
0.6372	Remote Similarity	NPD7100	Approved
0.6372	Remote Similarity	NPD7101	Approved
0.6364	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6926	Approved
0.6364	Remote Similarity	NPD6924	Approved
0.6355	Remote Similarity	NPD4730	Approved
0.6355	Remote Similarity	NPD5128	Approved
0.6355	Remote Similarity	NPD4729	Approved
0.6344	Remote Similarity	NPD6435	Approved
0.6344	Remote Similarity	NPD4270	Approved
0.6344	Remote Similarity	NPD4269	Approved
0.6327	Remote Similarity	NPD5692	Phase 3
0.6325	Remote Similarity	NPD6616	Approved
0.6322	Remote Similarity	NPD4243	Approved
0.6321	Remote Similarity	NPD6008	Approved
0.6316	Remote Similarity	NPD6054	Approved
0.6316	Remote Similarity	NPD6059	Approved
0.6304	Remote Similarity	NPD4819	Approved
0.6304	Remote Similarity	NPD4821	Approved
0.6304	Remote Similarity	NPD4822	Approved
0.6304	Remote Similarity	NPD4820	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