NPASS Compound

Structure

NPC212918 OpenBabel07101718312D 21 24 0 0 1 0 0 0 0 0999 V2000 0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 6 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.23
Volume:	323.768
LogP:	5.739
LogD:	4.967
LogS:	-6.064
# Rotatable Bonds:	0
TPSA:	13.14
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.594
Synthetic Accessibility Score:	4.142
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.797
MDCK Permeability:	1.3139690054231323e-05
Pgp-inhibitor:	0.778
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.896
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	96.14263153076172%
Volume Distribution (VD):	2.168
Pgp-substrate:	2.776550054550171%

ADMET: Metabolism

CYP1A2-inhibitor:	0.194
CYP1A2-substrate:	0.421
CYP2C19-inhibitor:	0.316
CYP2C19-substrate:	0.822
CYP2C9-inhibitor:	0.264
CYP2C9-substrate:	0.416
CYP2D6-inhibitor:	0.802
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.509
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	10.971
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.636
Skin Sensitization:	0.319
Carcinogencity:	0.803
Eye Corrosion:	0.136
Eye Irritation:	0.614
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC212918

Natural Product ID:	NPC212918
*Common Name:**	Spongia-13(16),14-Diene
IUPAC Name:	(3bR,5aS,9aS,9bR)-3b,6,6,9a-tetramethyl-5,5a,7,8,9,9b,10,11-octahydro-4H-naphtho[2,1-e][2]benzofuran
Synonyms:
Standard InCHIKey:	YMOPWLIPDPZTLZ-ZULIPRJHSA-N
Standard InCHI:	InChI=1S/C20H30O/c1-18(2)9-5-10-20(4)16(18)8-11-19(3)15-13-21-12-14(15)6-7-17(19)20/h12-13,16-17H,5-11H2,1-4H3/t16-,17-,19-,20-/m0/s1
SMILES:	CC1(C)CCC[C@@]2(C)[C@H]1CC[C@@]1(C)c3cocc3CC[C@H]21
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446647
PubChem CID:	10968137
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002550] Isocopalane and spongiane 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
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tongoa, Vanuatu Islands	1996	PMID[10757711]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662110]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497946]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tong-Yong City in the South Sea, Korea	n.a.	PMID[16905319]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17567172]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988093]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18407692]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[24992702]

☑ 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
Cell Line	1
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3511	Individual Protein	Thyrotropin-releasing hormone receptor 2	Rattus norvegicus	IC50	=	1000000.0	nM	PMID[574295]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC100	=	120.0	ug ml-1	PMID[574296]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	Activity	=	60.0	ug ml-1	PMID[574296]

☑ 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 NPC212918 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	381
0.1-0.2	1530
0.2-0.3	3472
0.3-0.4	8900
0.4-0.5	13480
0.5-0.6	12046
0.6-0.7	2449
0.7-0.8	358
0.8-0.85	47
0.85-0.9	24
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9561	High Similarity	NPC36255
0.9478	High Similarity	NPC272899
0.9397	High Similarity	NPC130275
0.9397	High Similarity	NPC83115
0.9316	High Similarity	NPC303010
0.9316	High Similarity	NPC230979
0.9083	High Similarity	NPC476917
0.9083	High Similarity	NPC327527
0.9008	High Similarity	NPC223063
0.9008	High Similarity	NPC120836
0.9008	High Similarity	NPC198904
0.8983	High Similarity	NPC16922
0.8974	High Similarity	NPC97566
0.8947	High Similarity	NPC150895
0.8934	High Similarity	NPC476925
0.8917	High Similarity	NPC74612
0.8908	High Similarity	NPC178382
0.8833	High Similarity	NPC179354
0.877	High Similarity	NPC477040
0.876	High Similarity	NPC46536
0.876	High Similarity	NPC23086
0.876	High Similarity	NPC138139
0.864	High Similarity	NPC471995
0.8618	High Similarity	NPC112706
0.8618	High Similarity	NPC207294
0.8618	High Similarity	NPC477123
0.8618	High Similarity	NPC477966
0.8559	High Similarity	NPC243704
0.8537	High Similarity	NPC83178
0.8516	High Similarity	NPC214572
0.8468	Intermediate Similarity	NPC477039
0.8468	Intermediate Similarity	NPC329707
0.845	Intermediate Similarity	NPC310043
0.845	Intermediate Similarity	NPC4764
0.845	Intermediate Similarity	NPC307401
0.843	Intermediate Similarity	NPC317217
0.843	Intermediate Similarity	NPC477967
0.8425	Intermediate Similarity	NPC471006
0.8413	Intermediate Similarity	NPC89133
0.8413	Intermediate Similarity	NPC61788
0.84	Intermediate Similarity	NPC59502
0.839	Intermediate Similarity	NPC59035
0.839	Intermediate Similarity	NPC79202
0.8359	Intermediate Similarity	NPC471998
0.8321	Intermediate Similarity	NPC202260
0.8295	Intermediate Similarity	NPC476947
0.8293	Intermediate Similarity	NPC477965
0.8293	Intermediate Similarity	NPC477038
0.8281	Intermediate Similarity	NPC218838
0.8268	Intermediate Similarity	NPC298190
0.8244	Intermediate Similarity	NPC476943
0.8244	Intermediate Similarity	NPC471996
0.8231	Intermediate Similarity	NPC46896
0.8226	Intermediate Similarity	NPC471074
0.8226	Intermediate Similarity	NPC473885
0.8168	Intermediate Similarity	NPC42400
0.8168	Intermediate Similarity	NPC310830
0.8154	Intermediate Similarity	NPC158525
0.814	Intermediate Similarity	NPC293253
0.8134	Intermediate Similarity	NPC62103
0.8134	Intermediate Similarity	NPC20578
0.8134	Intermediate Similarity	NPC263337
0.812	Intermediate Similarity	NPC277525
0.812	Intermediate Similarity	NPC56197
0.8099	Intermediate Similarity	NPC87466
0.8095	Intermediate Similarity	NPC290955
0.8095	Intermediate Similarity	NPC246392
0.8092	Intermediate Similarity	NPC146872
0.8031	Intermediate Similarity	NPC26532
0.8015	Intermediate Similarity	NPC92941
0.8	Intermediate Similarity	NPC470740
0.8	Intermediate Similarity	NPC243269
0.7985	Intermediate Similarity	NPC67003
0.797	Intermediate Similarity	NPC220094
0.7969	Intermediate Similarity	NPC208389
0.7956	Intermediate Similarity	NPC41182
0.7941	Intermediate Similarity	NPC103134
0.7926	Intermediate Similarity	NPC205765
0.7923	Intermediate Similarity	NPC471817
0.791	Intermediate Similarity	NPC90953
0.7899	Intermediate Similarity	NPC22678
0.7895	Intermediate Similarity	NPC470742
0.7891	Intermediate Similarity	NPC279877
0.7883	Intermediate Similarity	NPC476944
0.7883	Intermediate Similarity	NPC142113
0.7883	Intermediate Similarity	NPC238843
0.7883	Intermediate Similarity	NPC199044
0.7879	Intermediate Similarity	NPC324117
0.7869	Intermediate Similarity	NPC208906
0.7869	Intermediate Similarity	NPC144745
0.7868	Intermediate Similarity	NPC52412
0.7868	Intermediate Similarity	NPC121158
0.7851	Intermediate Similarity	NPC28054
0.7842	Intermediate Similarity	NPC216755
0.7842	Intermediate Similarity	NPC71821
0.7836	Intermediate Similarity	NPC236532
0.7826	Intermediate Similarity	NPC290038
0.7826	Intermediate Similarity	NPC185456
0.7826	Intermediate Similarity	NPC114513
0.7826	Intermediate Similarity	NPC245522
0.781	Intermediate Similarity	NPC476946
0.781	Intermediate Similarity	NPC243577
0.781	Intermediate Similarity	NPC267632
0.7795	Intermediate Similarity	NPC300098
0.7795	Intermediate Similarity	NPC290193
0.7786	Intermediate Similarity	NPC471007
0.7786	Intermediate Similarity	NPC473982
0.777	Intermediate Similarity	NPC233763
0.777	Intermediate Similarity	NPC471292
0.777	Intermediate Similarity	NPC470999
0.777	Intermediate Similarity	NPC478166
0.777	Intermediate Similarity	NPC262198
0.7754	Intermediate Similarity	NPC251865
0.7742	Intermediate Similarity	NPC137710
0.7737	Intermediate Similarity	NPC473152
0.7724	Intermediate Similarity	NPC227660
0.7721	Intermediate Similarity	NPC90296
0.7721	Intermediate Similarity	NPC148374
0.7717	Intermediate Similarity	NPC118853
0.7717	Intermediate Similarity	NPC188377
0.7717	Intermediate Similarity	NPC65735
0.7714	Intermediate Similarity	NPC281398
0.7714	Intermediate Similarity	NPC302987
0.7714	Intermediate Similarity	NPC471174
0.7705	Intermediate Similarity	NPC205523
0.7704	Intermediate Similarity	NPC177262
0.7698	Intermediate Similarity	NPC5676
0.7698	Intermediate Similarity	NPC56731
0.7681	Intermediate Similarity	NPC205071
0.7681	Intermediate Similarity	NPC64568
0.7676	Intermediate Similarity	NPC228842
0.7676	Intermediate Similarity	NPC212257
0.7674	Intermediate Similarity	NPC319140
0.7674	Intermediate Similarity	NPC95567
0.7667	Intermediate Similarity	NPC105249
0.7664	Intermediate Similarity	NPC20500
0.7647	Intermediate Similarity	NPC233707
0.7643	Intermediate Similarity	NPC62799
0.7643	Intermediate Similarity	NPC346
0.7642	Intermediate Similarity	NPC45536
0.7612	Intermediate Similarity	NPC209858
0.7606	Intermediate Similarity	NPC470998
0.7606	Intermediate Similarity	NPC95526
0.7606	Intermediate Similarity	NPC234494
0.7606	Intermediate Similarity	NPC471001
0.76	Intermediate Similarity	NPC473969
0.7589	Intermediate Similarity	NPC250228
0.7589	Intermediate Similarity	NPC10088
0.7589	Intermediate Similarity	NPC470941
0.7589	Intermediate Similarity	NPC255414
0.7589	Intermediate Similarity	NPC221809
0.7581	Intermediate Similarity	NPC217180
0.7581	Intermediate Similarity	NPC312525
0.7569	Intermediate Similarity	NPC472672
0.7569	Intermediate Similarity	NPC294511
0.7569	Intermediate Similarity	NPC121615
0.7563	Intermediate Similarity	NPC473356
0.7563	Intermediate Similarity	NPC471521
0.7554	Intermediate Similarity	NPC223415
0.7554	Intermediate Similarity	NPC470741
0.7552	Intermediate Similarity	NPC159927
0.7552	Intermediate Similarity	NPC196864
0.7552	Intermediate Similarity	NPC476122
0.7552	Intermediate Similarity	NPC477404
0.7552	Intermediate Similarity	NPC470997
0.7552	Intermediate Similarity	NPC472298
0.7552	Intermediate Similarity	NPC46551
0.7552	Intermediate Similarity	NPC469335
0.7552	Intermediate Similarity	NPC196846
0.7535	Intermediate Similarity	NPC476942
0.7535	Intermediate Similarity	NPC476941
0.7535	Intermediate Similarity	NPC93666
0.7535	Intermediate Similarity	NPC19747
0.7518	Intermediate Similarity	NPC97904
0.7518	Intermediate Similarity	NPC474722
0.7518	Intermediate Similarity	NPC276676
0.7517	Intermediate Similarity	NPC302054
0.7517	Intermediate Similarity	NPC34421
0.7517	Intermediate Similarity	NPC253201
0.7517	Intermediate Similarity	NPC98206
0.7517	Intermediate Similarity	NPC237259
0.75	Intermediate Similarity	NPC471000
0.75	Intermediate Similarity	NPC144010
0.75	Intermediate Similarity	NPC177331
0.75	Intermediate Similarity	NPC170604
0.75	Intermediate Similarity	NPC215109
0.75	Intermediate Similarity	NPC272590
0.7483	Intermediate Similarity	NPC472654
0.7483	Intermediate Similarity	NPC470790
0.7483	Intermediate Similarity	NPC470791
0.7483	Intermediate Similarity	NPC195325
0.7483	Intermediate Similarity	NPC211625
0.7483	Intermediate Similarity	NPC125182
0.7483	Intermediate Similarity	NPC69647
0.7466	Intermediate Similarity	NPC25351
0.7465	Intermediate Similarity	NPC476938
0.7465	Intermediate Similarity	NPC476937
0.7464	Intermediate Similarity	NPC18904
0.7448	Intermediate Similarity	NPC471002
0.7448	Intermediate Similarity	NPC33938

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 NPC212918 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	1036
0.2-0.3	1864
0.3-0.4	3049
0.4-0.5	1982
0.5-0.6	761
0.6-0.7	92
0.7-0.8	3
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
0.7466	Intermediate Similarity	NPD5761	Phase 2
0.7466	Intermediate Similarity	NPD5760	Phase 2
0.7391	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6273	Approved
0.7181	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD8032	Phase 2
0.7099	Intermediate Similarity	NPD3972	Approved
0.6992	Remote Similarity	NPD1876	Approved
0.6917	Remote Similarity	NPD5327	Phase 3
0.6901	Remote Similarity	NPD1471	Phase 3
0.6894	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7003	Approved
0.685	Remote Similarity	NPD1241	Discontinued
0.6818	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5585	Approved
0.6765	Remote Similarity	NPD2798	Approved
0.6759	Remote Similarity	NPD4628	Phase 3
0.6739	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD4140	Approved
0.6691	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD6832	Phase 2
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD2344	Approved
0.6643	Remote Similarity	NPD2799	Discontinued
0.6642	Remote Similarity	NPD1281	Approved
0.6623	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD17	Approved
0.6614	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2796	Approved
0.6596	Remote Similarity	NPD4307	Phase 2
0.6596	Remote Similarity	NPD2979	Phase 3
0.6575	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2313	Discontinued
0.6569	Remote Similarity	NPD3266	Approved
0.6569	Remote Similarity	NPD3267	Approved
0.6567	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6764	Approved
0.6564	Remote Similarity	NPD6765	Approved
0.6544	Remote Similarity	NPD4359	Approved
0.6513	Remote Similarity	NPD7458	Discontinued
0.6496	Remote Similarity	NPD1283	Approved
0.649	Remote Similarity	NPD3869	Phase 3
0.649	Remote Similarity	NPD3873	Phase 3
0.6486	Remote Similarity	NPD2309	Approved
0.6483	Remote Similarity	NPD6099	Approved
0.6483	Remote Similarity	NPD6100	Approved
0.6471	Remote Similarity	NPD1608	Approved
0.6467	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD8434	Phase 2
0.6454	Remote Similarity	NPD3268	Approved
0.6443	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD4618	Approved
0.6434	Remote Similarity	NPD6355	Discontinued
0.6434	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5735	Approved
0.6434	Remote Similarity	NPD4622	Approved
0.6419	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD4110	Phase 3
0.6418	Remote Similarity	NPD5691	Approved
0.6418	Remote Similarity	NPD3024	Approved
0.6418	Remote Similarity	NPD3025	Approved
0.6414	Remote Similarity	NPD4308	Phase 3
0.6414	Remote Similarity	NPD3748	Approved
0.6412	Remote Similarity	NPD5951	Approved
0.6407	Remote Similarity	NPD6785	Approved
0.6407	Remote Similarity	NPD6784	Approved
0.6389	Remote Similarity	NPD6353	Approved
0.6387	Remote Similarity	NPD6280	Approved
0.6387	Remote Similarity	NPD6279	Approved
0.6385	Remote Similarity	NPD5535	Approved
0.6383	Remote Similarity	NPD7008	Discontinued
0.6382	Remote Similarity	NPD920	Approved
0.637	Remote Similarity	NPD3019	Approved
0.637	Remote Similarity	NPD4477	Approved
0.637	Remote Similarity	NPD2531	Phase 2
0.637	Remote Similarity	NPD2438	Suspended
0.637	Remote Similarity	NPD4476	Approved
0.6364	Remote Similarity	NPD3142	Approved
0.6364	Remote Similarity	NPD3140	Approved
0.6358	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD1243	Approved
0.6351	Remote Similarity	NPD2800	Approved
0.6345	Remote Similarity	NPD5689	Approved
0.6345	Remote Similarity	NPD5688	Approved
0.6343	Remote Similarity	NPD1894	Discontinued
0.6338	Remote Similarity	NPD6798	Discontinued
0.6338	Remote Similarity	NPD3764	Approved
0.6331	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD2182	Approved
0.6324	Remote Similarity	NPD3026	Approved
0.6324	Remote Similarity	NPD3023	Approved
0.6319	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD8127	Discontinued
0.6306	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD3226	Approved
0.6294	Remote Similarity	NPD6663	Approved
0.6294	Remote Similarity	NPD4870	Approved
0.6286	Remote Similarity	NPD4624	Approved
0.6284	Remote Similarity	NPD2897	Discontinued
0.6268	Remote Similarity	NPD7095	Approved
0.6266	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD1551	Phase 2
0.6258	Remote Similarity	NPD6599	Discontinued
0.6258	Remote Similarity	NPD7028	Phase 2
0.625	Remote Similarity	NPD5494	Approved
0.625	Remote Similarity	NPD1778	Approved
0.625	Remote Similarity	NPD2932	Approved
0.625	Remote Similarity	NPD2532	Approved
0.625	Remote Similarity	NPD2533	Approved
0.625	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2534	Approved
0.6242	Remote Similarity	NPD7819	Suspended
0.6241	Remote Similarity	NPD5736	Approved
0.6241	Remote Similarity	NPD7157	Approved
0.6224	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6005	Phase 3
0.6216	Remote Similarity	NPD6002	Phase 3
0.6216	Remote Similarity	NPD6004	Phase 3
0.6216	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.621	Remote Similarity	NPD1238	Approved
0.6207	Remote Similarity	NPD1933	Approved
0.62	Remote Similarity	NPD3750	Approved
0.62	Remote Similarity	NPD8166	Discontinued
0.6181	Remote Similarity	NPD6233	Phase 2
0.6178	Remote Similarity	NPD7577	Discontinued
0.6176	Remote Similarity	NPD3445	Approved
0.6176	Remote Similarity	NPD3443	Approved
0.6176	Remote Similarity	NPD3444	Approved
0.6174	Remote Similarity	NPD4534	Discontinued
0.6172	Remote Similarity	NPD3134	Approved
0.617	Remote Similarity	NPD1019	Discontinued
0.6169	Remote Similarity	NPD7427	Discontinued
0.6168	Remote Similarity	NPD6559	Discontinued
0.6164	Remote Similarity	NPD7768	Phase 2
0.6159	Remote Similarity	NPD3887	Approved
0.6159	Remote Similarity	NPD6287	Discontinued
0.6159	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD2935	Discontinued
0.6148	Remote Similarity	NPD7644	Approved
0.6144	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD3620	Phase 2
0.6138	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6858	Approved
0.6136	Remote Similarity	NPD7094	Approved
0.6131	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD4626	Approved
0.6125	Remote Similarity	NPD3749	Approved
0.6121	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD7236	Approved
0.6118	Remote Similarity	NPD7440	Discontinued
0.6115	Remote Similarity	NPD9717	Approved
0.6115	Remote Similarity	NPD7411	Suspended
0.6115	Remote Similarity	NPD6677	Suspended
0.6111	Remote Similarity	NPD7294	Phase 1
0.6111	Remote Similarity	NPD6959	Discontinued
0.6111	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD6581	Approved
0.6103	Remote Similarity	NPD6580	Approved
0.6099	Remote Similarity	NPD1203	Approved
0.6096	Remote Similarity	NPD3657	Discovery
0.609	Remote Similarity	NPD2651	Approved
0.609	Remote Similarity	NPD2649	Approved
0.6087	Remote Similarity	NPD3496	Discontinued
0.6087	Remote Similarity	NPD919	Approved
0.6084	Remote Similarity	NPD2614	Approved
0.6084	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD2684	Approved
0.6074	Remote Similarity	NPD6808	Phase 2
0.6069	Remote Similarity	NPD7713	Phase 3
0.6067	Remote Similarity	NPD5958	Discontinued
0.6067	Remote Similarity	NPD1549	Phase 2
0.6065	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD6651	Approved
0.6043	Remote Similarity	NPD1201	Approved
0.6043	Remote Similarity	NPD1611	Approved
0.6039	Remote Similarity	NPD4662	Approved
0.6039	Remote Similarity	NPD4661	Approved
0.6038	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD5451	Approved
0.6028	Remote Similarity	NPD6696	Suspended
0.6027	Remote Similarity	NPD4060	Phase 1
0.6024	Remote Similarity	NPD7177	Discontinued
0.6016	Remote Similarity	NPD164	Approved
0.6016	Remote Similarity	NPD5909	Discontinued
0.6014	Remote Similarity	NPD9494	Approved
0.6014	Remote Similarity	NPD7097	Phase 1
0.6013	Remote Similarity	NPD5889	Approved
0.6013	Remote Similarity	NPD5890	Approved
0.6013	Remote Similarity	NPD6873	Phase 2

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