NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1324.85
Volume:	1365.354
LogP:	-0.282
LogD:	2.149
LogS:	-2.989
# Rotatable Bonds:	51
TPSA:	463.52
# H-Bond Aceptor:	24
# H-Bond Donor:	22
# Rings:	2
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.022
Synthetic Accessibility Score:	7.706
Fsp3:	0.853
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.925
MDCK Permeability:	0.00016771252558100969
Pgp-inhibitor:	0.0
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	84.38005828857422%
Volume Distribution (VD):	-0.052
Pgp-substrate:	5.6741743087768555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.024
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.989
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.018
CYP3A4-inhibitor:	0.0
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	0.136
Half-life (T1/2):	0.059

ADMET: Toxicity

hERG Blockers:	0.102
Human Hepatotoxicity (H-HT):	0.403
Drug-inuced Liver Injury (DILI):	0.004
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.822
Maximum Recommended Daily Dose:	0.806
Skin Sensitization:	0.017
Carcinogencity:	0.002
Eye Corrosion:	0.003
Eye Irritation:	0.001
Respiratory Toxicity:	0.176

Download Data

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

Natural Product: NPC477385

Natural Product ID:	NPC477385
*Common Name:**	(E)-31-[6-[6-[6-[(3E,14E)-1,2-dihydroxyheptadeca-3,14,16-trienyl]-4,5-dihydroxyoxan-2-yl]-1,5,6-trihydroxy-4-methylidenehexyl]-3,4,5-trihydroxyoxan-2-yl]-16,21,28-trimethylhentriacont-4-ene-1,2,6,10,14,17,18,22,23,24,29,30-dodecol
IUPAC Name:	(E)-31-[6-[6-[6-[(3E,14E)-1,2-dihydroxyheptadeca-3,14,16-trienyl]-4,5-dihydroxyoxan-2-yl]-1,5,6-trihydroxy-4-methylidenehexyl]-3,4,5-trihydroxyoxan-2-yl]-16,21,28-trimethylhentriacont-4-ene-1,2,6,10,14,17,18,22,23,24,29,30-dodecol
Synonyms:
Standard InCHIKey:	GYPJDXBMGANEHW-DTUMZGMKSA-N
Standard InCHI:	InChI=1S/C68H124O24/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-30-49(75)61(85)68-62(86)53(79)38-54(92-68)63(87)59(83)42(4)33-35-51(77)67-66(90)65(89)64(88)55(91-67)37-52(78)56(80)40(2)23-19-31-48(74)60(84)58(82)41(3)32-34-50(76)57(81)43(5)36-46(72)28-21-26-44(70)24-20-25-45(71)27-22-29-47(73)39-69/h6-8,18,22,27,30,40-41,43-90H,1,4,9-17,19-21,23-26,28-29,31-39H2,2-3,5H3/b8-7+,27-22+,30-18+
SMILES:	CC(CCCC(C(C(C(C)CCC(C(C(C)CC(CCCC(CCCC(/C=C/CC(CO)O)O)O)O)O)O)O)O)O)C(C(CC1C(C(C(C(O1)C(CCC(=C)C(C(C2CC(C(C(O2)C(C(/C=C/CCCCCCCCC/C=C/C=C)O)O)O)O)O)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	46919393
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002204] C-glycosyl compounds

*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
NPO26756	Karlodinium veneficum	Species	Kareniaceae	Eukaryota	n.a.	Delaware Inland Bays, USA	n.a.	PMID[20795740]
NPO26756	Karlodinium veneficum	Species	Kareniaceae	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
EC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		EC50	=	200	nM	PMID[20795740]

☑ 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 NPC477385 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	187
0.1-0.2	1130
0.2-0.3	4190
0.3-0.4	10523
0.4-0.5	14470
0.5-0.6	9097
0.6-0.7	2839
0.7-0.8	242
0.8-0.85	4
0.85-0.9	1
0.9-0.95	3
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477390
0.95	High Similarity	NPC477387
0.95	High Similarity	NPC477389
0.9383	High Similarity	NPC477388
0.9383	High Similarity	NPC477386
0.8242	Intermediate Similarity	NPC475332
0.7957	Intermediate Similarity	NPC475653
0.7927	Intermediate Similarity	NPC476703
0.7849	Intermediate Similarity	NPC120299
0.7831	Intermediate Similarity	NPC477089
0.7805	Intermediate Similarity	NPC170148
0.7802	Intermediate Similarity	NPC109406
0.7778	Intermediate Similarity	NPC191323
0.7742	Intermediate Similarity	NPC255410
0.7738	Intermediate Similarity	NPC476701
0.7727	Intermediate Similarity	NPC311163
0.7722	Intermediate Similarity	NPC329989
0.7722	Intermediate Similarity	NPC239373
0.7717	Intermediate Similarity	NPC472198
0.7708	Intermediate Similarity	NPC473596
0.7692	Intermediate Similarity	NPC114172
0.7692	Intermediate Similarity	NPC73603
0.7692	Intermediate Similarity	NPC476084
0.7692	Intermediate Similarity	NPC206679
0.7692	Intermediate Similarity	NPC476075
0.7692	Intermediate Similarity	NPC471324
0.7667	Intermediate Similarity	NPC49783
0.7653	Intermediate Similarity	NPC315070
0.764	Intermediate Similarity	NPC199382
0.7634	Intermediate Similarity	NPC300710
0.7619	Intermediate Similarity	NPC475980
0.7619	Intermediate Similarity	NPC68119
0.7619	Intermediate Similarity	NPC13823
0.7614	Intermediate Similarity	NPC298595
0.7609	Intermediate Similarity	NPC159092
0.7604	Intermediate Similarity	NPC2313
0.7604	Intermediate Similarity	NPC471637
0.7604	Intermediate Similarity	NPC154132
0.7604	Intermediate Similarity	NPC475157
0.7604	Intermediate Similarity	NPC475655
0.7604	Intermediate Similarity	NPC57586
0.759	Intermediate Similarity	NPC256720
0.759	Intermediate Similarity	NPC236228
0.7582	Intermediate Similarity	NPC313670
0.7582	Intermediate Similarity	NPC177668
0.7582	Intermediate Similarity	NPC3952
0.7561	Intermediate Similarity	NPC24590
0.7561	Intermediate Similarity	NPC190859
0.7558	Intermediate Similarity	NPC315731
0.7558	Intermediate Similarity	NPC474894
0.7556	Intermediate Similarity	NPC231784
0.7556	Intermediate Similarity	NPC248312
0.7553	Intermediate Similarity	NPC173329
0.7553	Intermediate Similarity	NPC288350
0.7527	Intermediate Similarity	NPC159698
0.75	Intermediate Similarity	NPC74722
0.75	Intermediate Similarity	NPC472199
0.75	Intermediate Similarity	NPC472197
0.75	Intermediate Similarity	NPC64348
0.75	Intermediate Similarity	NPC304690
0.7473	Intermediate Similarity	NPC128066
0.7473	Intermediate Similarity	NPC115607
0.7473	Intermediate Similarity	NPC133450
0.7468	Intermediate Similarity	NPC163290
0.7449	Intermediate Similarity	NPC197736
0.7444	Intermediate Similarity	NPC313658
0.7444	Intermediate Similarity	NPC86005
0.7444	Intermediate Similarity	NPC316138
0.7439	Intermediate Similarity	NPC476709
0.7419	Intermediate Similarity	NPC238090
0.7419	Intermediate Similarity	NPC472196
0.7419	Intermediate Similarity	NPC472195
0.7416	Intermediate Similarity	NPC471494
0.7412	Intermediate Similarity	NPC181838
0.7412	Intermediate Similarity	NPC137345
0.7391	Intermediate Similarity	NPC477866
0.7391	Intermediate Similarity	NPC477865
0.7386	Intermediate Similarity	NPC320548
0.7375	Intermediate Similarity	NPC305698
0.7368	Intermediate Similarity	NPC57664
0.7356	Intermediate Similarity	NPC184208
0.7356	Intermediate Similarity	NPC8538
0.7349	Intermediate Similarity	NPC471525
0.7342	Intermediate Similarity	NPC267027
0.7342	Intermediate Similarity	NPC311736
0.734	Intermediate Similarity	NPC256368
0.7333	Intermediate Similarity	NPC281316
0.7333	Intermediate Similarity	NPC247826
0.7326	Intermediate Similarity	NPC471537
0.7312	Intermediate Similarity	NPC302584
0.7303	Intermediate Similarity	NPC83702
0.7294	Intermediate Similarity	NPC40049
0.7292	Intermediate Similarity	NPC240372
0.7284	Intermediate Similarity	NPC16964
0.7284	Intermediate Similarity	NPC472947
0.7283	Intermediate Similarity	NPC97103
0.7283	Intermediate Similarity	NPC299527
0.7273	Intermediate Similarity	NPC20072
0.7255	Intermediate Similarity	NPC133625
0.7253	Intermediate Similarity	NPC477959
0.725	Intermediate Similarity	NPC259299
0.725	Intermediate Similarity	NPC82337
0.7241	Intermediate Similarity	NPC100697
0.7237	Intermediate Similarity	NPC122239
0.7234	Intermediate Similarity	NPC478036
0.7234	Intermediate Similarity	NPC478037
0.7229	Intermediate Similarity	NPC55652
0.7228	Intermediate Similarity	NPC257964
0.7216	Intermediate Similarity	NPC203627
0.7216	Intermediate Similarity	NPC65700
0.7215	Intermediate Similarity	NPC308844
0.72	Intermediate Similarity	NPC54521
0.72	Intermediate Similarity	NPC57065
0.72	Intermediate Similarity	NPC109792
0.72	Intermediate Similarity	NPC470768
0.7191	Intermediate Similarity	NPC44261
0.7188	Intermediate Similarity	NPC90583
0.7176	Intermediate Similarity	NPC469880
0.7159	Intermediate Similarity	NPC320525
0.7158	Intermediate Similarity	NPC469491
0.7157	Intermediate Similarity	NPC193765
0.7157	Intermediate Similarity	NPC126147
0.7143	Intermediate Similarity	NPC61527
0.7143	Intermediate Similarity	NPC469942
0.7143	Intermediate Similarity	NPC255143
0.7143	Intermediate Similarity	NPC472379
0.7129	Intermediate Similarity	NPC470767
0.7129	Intermediate Similarity	NPC476738
0.7129	Intermediate Similarity	NPC476740
0.7129	Intermediate Similarity	NPC470763
0.7128	Intermediate Similarity	NPC471453
0.7126	Intermediate Similarity	NPC233295
0.7126	Intermediate Similarity	NPC86971
0.7105	Intermediate Similarity	NPC226848
0.71	Intermediate Similarity	NPC99627
0.71	Intermediate Similarity	NPC473129
0.71	Intermediate Similarity	NPC162354
0.7097	Intermediate Similarity	NPC309310
0.7083	Intermediate Similarity	NPC476894
0.7071	Intermediate Similarity	NPC267510
0.7071	Intermediate Similarity	NPC169365
0.7071	Intermediate Similarity	NPC470434
0.7071	Intermediate Similarity	NPC197447
0.7065	Intermediate Similarity	NPC125142
0.7059	Intermediate Similarity	NPC313179
0.7059	Intermediate Similarity	NPC108682
0.7059	Intermediate Similarity	NPC171148
0.7059	Intermediate Similarity	NPC69383
0.7059	Intermediate Similarity	NPC472263
0.7059	Intermediate Similarity	NPC12696
0.7059	Intermediate Similarity	NPC469957
0.7059	Intermediate Similarity	NPC469959
0.7053	Intermediate Similarity	NPC320552
0.7053	Intermediate Similarity	NPC119379
0.7053	Intermediate Similarity	NPC474792
0.7053	Intermediate Similarity	NPC67398
0.7053	Intermediate Similarity	NPC310013
0.7053	Intermediate Similarity	NPC320089
0.7053	Intermediate Similarity	NPC91654
0.7045	Intermediate Similarity	NPC474592
0.7045	Intermediate Similarity	NPC133226
0.7045	Intermediate Similarity	NPC96362
0.7045	Intermediate Similarity	NPC470147
0.7045	Intermediate Similarity	NPC324772
0.7041	Intermediate Similarity	NPC476895
0.7041	Intermediate Similarity	NPC187761
0.7041	Intermediate Similarity	NPC308567
0.7041	Intermediate Similarity	NPC255592
0.7041	Intermediate Similarity	NPC261377
0.7041	Intermediate Similarity	NPC83895
0.7033	Intermediate Similarity	NPC290731
0.7033	Intermediate Similarity	NPC242233
0.703	Intermediate Similarity	NPC230948
0.703	Intermediate Similarity	NPC75608
0.703	Intermediate Similarity	NPC473734
0.7024	Intermediate Similarity	NPC130665
0.7024	Intermediate Similarity	NPC477085
0.7021	Intermediate Similarity	NPC327253
0.7011	Intermediate Similarity	NPC4436
0.7011	Intermediate Similarity	NPC3852
0.7011	Intermediate Similarity	NPC83351
0.7011	Intermediate Similarity	NPC167891
0.701	Intermediate Similarity	NPC288970
0.701	Intermediate Similarity	NPC210717
0.701	Intermediate Similarity	NPC98457
0.701	Intermediate Similarity	NPC103165
0.701	Intermediate Similarity	NPC12103
0.701	Intermediate Similarity	NPC472995
0.701	Intermediate Similarity	NPC165332
0.701	Intermediate Similarity	NPC195645
0.701	Intermediate Similarity	NPC180722
0.701	Intermediate Similarity	NPC475503
0.701	Intermediate Similarity	NPC227583
0.7	Intermediate Similarity	NPC470571
0.7	Intermediate Similarity	NPC231601
0.7	Intermediate Similarity	NPC272015
0.7	Intermediate Similarity	NPC250836
0.7	Intermediate Similarity	NPC471200
0.7	Intermediate Similarity	NPC473722
0.699	Remote Similarity	NPC473807

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 NPC477385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1293
0.2-0.3	3795
0.3-0.4	2512
0.4-0.5	1036
0.5-0.6	278
0.6-0.7	53
0.7-0.8	20
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
0.7778	Intermediate Similarity	NPD7838	Discovery
0.7692	Intermediate Similarity	NPD7983	Approved
0.764	Intermediate Similarity	NPD7524	Approved
0.7579	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6695	Phase 3
0.7253	Intermediate Similarity	NPD7750	Discontinued
0.7204	Intermediate Similarity	NPD6698	Approved
0.7204	Intermediate Similarity	NPD46	Approved
0.7126	Intermediate Similarity	NPD6929	Approved
0.7059	Intermediate Similarity	NPD8264	Approved
0.7053	Intermediate Similarity	NPD5778	Approved
0.7053	Intermediate Similarity	NPD5779	Approved
0.7045	Intermediate Similarity	NPD6930	Phase 2
0.7045	Intermediate Similarity	NPD6931	Approved
0.7045	Intermediate Similarity	NPD7514	Phase 3
0.7045	Intermediate Similarity	NPD7332	Phase 2
0.7011	Intermediate Similarity	NPD7145	Approved
0.701	Intermediate Similarity	NPD7839	Suspended
0.6966	Remote Similarity	NPD6902	Approved
0.6952	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6925	Approved
0.6897	Remote Similarity	NPD5776	Phase 2
0.6782	Remote Similarity	NPD6933	Approved
0.6771	Remote Similarity	NPD7087	Discontinued
0.6771	Remote Similarity	NPD7637	Suspended
0.6733	Remote Similarity	NPD5344	Discontinued
0.6705	Remote Similarity	NPD6932	Approved
0.6667	Remote Similarity	NPD6893	Approved
0.6634	Remote Similarity	NPD6648	Approved
0.6629	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4732	Discontinued
0.6593	Remote Similarity	NPD6898	Phase 1
0.6562	Remote Similarity	NPD6101	Approved
0.6562	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6926	Approved
0.6552	Remote Similarity	NPD6924	Approved
0.6549	Remote Similarity	NPD8517	Approved
0.6549	Remote Similarity	NPD8513	Phase 3
0.6549	Remote Similarity	NPD8515	Approved
0.6549	Remote Similarity	NPD8516	Approved
0.6484	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6640	Phase 3
0.6452	Remote Similarity	NPD7154	Phase 3
0.6429	Remote Similarity	NPD6411	Approved
0.642	Remote Similarity	NPD368	Approved
0.6395	Remote Similarity	NPD7143	Approved
0.6395	Remote Similarity	NPD7144	Approved
0.6379	Remote Similarity	NPD8340	Approved
0.6379	Remote Similarity	NPD8299	Approved
0.6379	Remote Similarity	NPD8342	Approved
0.6379	Remote Similarity	NPD8341	Approved
0.6374	Remote Similarity	NPD6683	Phase 2
0.6355	Remote Similarity	NPD6686	Approved
0.6354	Remote Similarity	NPD4251	Approved
0.6354	Remote Similarity	NPD4250	Approved
0.6327	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7136	Phase 2
0.6322	Remote Similarity	NPD7152	Approved
0.6322	Remote Similarity	NPD7151	Approved
0.6322	Remote Similarity	NPD7150	Approved
0.6304	Remote Similarity	NPD4820	Approved
0.6304	Remote Similarity	NPD4822	Approved
0.6304	Remote Similarity	NPD7509	Discontinued
0.6304	Remote Similarity	NPD4819	Approved
0.6304	Remote Similarity	NPD4821	Approved
0.6282	Remote Similarity	NPD342	Phase 1
0.6279	Remote Similarity	NPD6923	Approved
0.6279	Remote Similarity	NPD6922	Approved
0.6271	Remote Similarity	NPD8074	Phase 3
0.6271	Remote Similarity	NPD8448	Approved
0.6264	Remote Similarity	NPD4271	Approved
0.6264	Remote Similarity	NPD4268	Approved
0.625	Remote Similarity	NPD4249	Approved
0.6214	Remote Similarity	NPD4225	Approved
0.6195	Remote Similarity	NPD7505	Discontinued
0.6186	Remote Similarity	NPD8273	Phase 1
0.6186	Remote Similarity	NPD8451	Approved
0.6154	Remote Similarity	NPD7829	Approved
0.6154	Remote Similarity	NPD7830	Approved
0.6121	Remote Similarity	NPD8033	Approved
0.6121	Remote Similarity	NPD7503	Approved
0.6121	Remote Similarity	NPD8444	Approved
0.6111	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5362	Discontinued
0.6105	Remote Similarity	NPD6110	Phase 1
0.6042	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD8377	Approved
0.6034	Remote Similarity	NPD8294	Approved
0.6022	Remote Similarity	NPD7645	Phase 2
0.602	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4219	Approved
0.6	Remote Similarity	NPD3168	Discontinued
0.5984	Remote Similarity	NPD8390	Approved
0.5984	Remote Similarity	NPD8392	Approved
0.5984	Remote Similarity	NPD8391	Approved
0.5983	Remote Similarity	NPD8380	Approved
0.5983	Remote Similarity	NPD8378	Approved
0.5983	Remote Similarity	NPD8379	Approved
0.5983	Remote Similarity	NPD8296	Approved
0.5983	Remote Similarity	NPD8335	Approved
0.598	Remote Similarity	NPD5282	Discontinued
0.5963	Remote Similarity	NPD6412	Phase 2
0.5957	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7525	Registered
0.5946	Remote Similarity	NPD6371	Approved
0.5938	Remote Similarity	NPD5332	Approved
0.5938	Remote Similarity	NPD5331	Approved
0.5934	Remote Similarity	NPD7339	Approved
0.5934	Remote Similarity	NPD6942	Approved
0.5895	Remote Similarity	NPD4790	Discontinued
0.5882	Remote Similarity	NPD371	Approved
0.587	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7641	Discontinued
0.5862	Remote Similarity	NPD7327	Approved
0.5862	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7328	Approved
0.5854	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7639	Approved
0.5849	Remote Similarity	NPD7640	Approved
0.5833	Remote Similarity	NPD4270	Approved
0.5833	Remote Similarity	NPD6435	Approved
0.5833	Remote Similarity	NPD4269	Approved
0.5816	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7516	Approved
0.5804	Remote Similarity	NPD6421	Discontinued
0.5798	Remote Similarity	NPD5125	Phase 3
0.5798	Remote Similarity	NPD5126	Approved
0.5789	Remote Similarity	NPD8133	Approved
0.5763	Remote Similarity	NPD7741	Discontinued
0.5761	Remote Similarity	NPD8039	Approved
0.5758	Remote Similarity	NPD5786	Approved
0.5755	Remote Similarity	NPD7638	Approved
0.5752	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.575	Remote Similarity	NPD8328	Phase 3
0.5745	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6429	Approved
0.5702	Remote Similarity	NPD6430	Approved
0.5676	Remote Similarity	NPD6685	Approved
0.5667	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD5363	Approved
0.5641	Remote Similarity	NPD7115	Discovery
0.5641	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD7500	Approved
0.5641	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4252	Approved
0.5625	Remote Similarity	NPD5368	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