NPASS Compound

Structure

NPC476335 OpenBabel07101718232D 28 30 0 0 1 0 0 0 0 0999 V2000 2.9909 -0.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 -0.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5576 4.5451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2317 1.6455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3946 4.0618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6042 -1.5612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3840 0.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8159 1.0822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8835 2.6120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7205 1.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6586 0.2250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9454 0.2010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8934 0.8802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8835 1.6455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7205 3.0953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5576 1.6455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0464 1.1622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1635 1.5553 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5275 1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5576 2.6120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4833 0.8370 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0479 2.2867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4445 0.9381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7205 4.0618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3946 1.1622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3946 3.0953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1486 -0.9550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 12 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 13 2 0 0 0 0 11 22 1 0 0 0 0 12 17 1 0 0 0 0 12 22 1 6 0 0 0 13 19 1 0 0 0 0 15 20 2 0 0 0 0 15 25 1 0 0 0 0 16 20 1 0 0 0 0 16 26 1 0 0 0 0 17 14 1 1 0 0 0 17 18 1 0 0 0 0 18 19 1 6 0 0 0 18 21 1 0 0 0 0 19 23 2 0 0 0 0 20 27 1 0 0 0 0 21 22 1 1 0 0 0 21 24 1 0 0 0 0 22 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.19
Volume:	400.321
LogP:	2.317
LogD:	2.19
LogS:	-3.82
# Rotatable Bonds:	7
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.724
Synthetic Accessibility Score:	4.98
Fsp3:	0.5
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:	-4.559
MDCK Permeability:	1.5987205188139342e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.233

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.299
Plasma Protein Binding (PPB):	75.97953033447266%
Volume Distribution (VD):	1.239
Pgp-substrate:	13.439533233642578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.298
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.652
CYP3A4-inhibitor:	0.824
CYP3A4-substrate:	0.859

ADMET: Excretion

Clearance (CL):	8.919
Half-life (T1/2):	0.546

ADMET: Toxicity

hERG Blockers:	0.174
Human Hepatotoxicity (H-HT):	0.489
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.695
Maximum Recommended Daily Dose:	0.43
Skin Sensitization:	0.423
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC476335

Natural Product ID:	NPC476335
*Common Name:**	Ocophylol C
IUPAC Name:	(1S,5S,6R,7R,8R)-8-hydroxy-5-methoxy-6-methyl-3-prop-2-enyl-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-en-2-one
Synonyms:	Ocophylol C
Standard InCHIKey:	OXBOQKXJZRJDAW-UXPMNEGVSA-N
Standard InCHI:	InChI=1S/C22H28O6/c1-7-8-13-11-22(28-6)12(2)17(18(19(13)23)21(22)24)14-9-15(25-3)20(27-5)16(10-14)26-4/h7,9-12,17-18,21,24H,1,8H2,2-6H3/t12-,17+,18-,21-,22-/m1/s1
SMILES:	C=CCC1=C[C@]2(OC)[C@@H]([C@@H](C1=O)[C@@H]([C@H]2C)c1cc(OC)c(c(c1)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL570318
PubChem CID:	45487119
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19548690]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO27964	Nectandra amazonum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27964	Nectandra amazonum	Species	Lauraceae	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	6
Others	1

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	72100.0	nM	PMID[531152]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	245000.0	nM	PMID[531152]
NPT2	Others	Unspecified		IC50	=	176000.0	nM	PMID[531152]
NPT2	Others	Unspecified		Ratio IC50	=	0.294	n.a.	PMID[531152]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2340.0	nM	PMID[531152]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	48600.0	nM	PMID[531152]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	999000.0	nM	PMID[531152]

☑ 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 NPC476335 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	368
0.1-0.2	1294
0.2-0.3	2973
0.3-0.4	7100
0.4-0.5	11014
0.5-0.6	5475
0.6-0.7	7937
0.7-0.8	6405
0.8-0.85	107
0.85-0.9	14
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9664	High Similarity	NPC476340
0.9653	High Similarity	NPC476359
0.9653	High Similarity	NPC476338
0.9536	High Similarity	NPC476337
0.9231	High Similarity	NPC476277
0.9205	High Similarity	NPC476364
0.92	High Similarity	NPC28724
0.9054	High Similarity	NPC476362
0.8797	High Similarity	NPC476244
0.8758	High Similarity	NPC62354
0.875	High Similarity	NPC474903
0.871	High Similarity	NPC25127
0.8701	High Similarity	NPC151425
0.8627	High Similarity	NPC472567
0.8608	High Similarity	NPC472565
0.8591	High Similarity	NPC476334
0.859	High Similarity	NPC287504
0.8553	High Similarity	NPC30890
0.8535	High Similarity	NPC476363
0.8526	High Similarity	NPC327225
0.8516	High Similarity	NPC163002
0.8497	Intermediate Similarity	NPC476336
0.8497	Intermediate Similarity	NPC30720
0.8435	Intermediate Similarity	NPC145769
0.8421	Intermediate Similarity	NPC46161
0.8421	Intermediate Similarity	NPC239608
0.84	Intermediate Similarity	NPC4796
0.8397	Intermediate Similarity	NPC472279
0.8375	Intermediate Similarity	NPC477410
0.8367	Intermediate Similarity	NPC327410
0.8344	Intermediate Similarity	NPC51681
0.8323	Intermediate Similarity	NPC77598
0.8313	Intermediate Similarity	NPC78071
0.8312	Intermediate Similarity	NPC212697
0.8293	Intermediate Similarity	NPC173292
0.8291	Intermediate Similarity	NPC470340
0.8291	Intermediate Similarity	NPC180944
0.8289	Intermediate Similarity	NPC46180
0.8282	Intermediate Similarity	NPC319200
0.8282	Intermediate Similarity	NPC124038
0.8282	Intermediate Similarity	NPC187491
0.8278	Intermediate Similarity	NPC322021
0.8278	Intermediate Similarity	NPC203351
0.8278	Intermediate Similarity	NPC474784
0.8266	Intermediate Similarity	NPC71385
0.8266	Intermediate Similarity	NPC230670
0.8261	Intermediate Similarity	NPC187792
0.825	Intermediate Similarity	NPC469474
0.8247	Intermediate Similarity	NPC207732
0.8235	Intermediate Similarity	NPC474966
0.8228	Intermediate Similarity	NPC46882
0.8228	Intermediate Similarity	NPC256406
0.8228	Intermediate Similarity	NPC132990
0.8224	Intermediate Similarity	NPC470991
0.8218	Intermediate Similarity	NPC112708
0.8217	Intermediate Similarity	NPC195763
0.8217	Intermediate Similarity	NPC142876
0.8217	Intermediate Similarity	NPC333691
0.8217	Intermediate Similarity	NPC40290
0.8217	Intermediate Similarity	NPC200060
0.8217	Intermediate Similarity	NPC69430
0.8217	Intermediate Similarity	NPC264550
0.8217	Intermediate Similarity	NPC264289
0.8217	Intermediate Similarity	NPC12854
0.8217	Intermediate Similarity	NPC139293
0.8214	Intermediate Similarity	NPC107739
0.8212	Intermediate Similarity	NPC470962
0.821	Intermediate Similarity	NPC155302
0.821	Intermediate Similarity	NPC161947
0.8199	Intermediate Similarity	NPC129684
0.8199	Intermediate Similarity	NPC299520
0.8194	Intermediate Similarity	NPC213482
0.8194	Intermediate Similarity	NPC472560
0.8194	Intermediate Similarity	NPC157133
0.8187	Intermediate Similarity	NPC255807
0.8187	Intermediate Similarity	NPC31018
0.8182	Intermediate Similarity	NPC15743
0.8182	Intermediate Similarity	NPC16353
0.8182	Intermediate Similarity	NPC128293
0.8182	Intermediate Similarity	NPC119589
0.8182	Intermediate Similarity	NPC119663
0.8182	Intermediate Similarity	NPC235610
0.8176	Intermediate Similarity	NPC323626
0.8176	Intermediate Similarity	NPC470337
0.8176	Intermediate Similarity	NPC268992
0.8176	Intermediate Similarity	NPC51824
0.8176	Intermediate Similarity	NPC470338
0.8176	Intermediate Similarity	NPC113608
0.8176	Intermediate Similarity	NPC324233
0.8171	Intermediate Similarity	NPC473711
0.8166	Intermediate Similarity	NPC23593
0.8165	Intermediate Similarity	NPC178048
0.8165	Intermediate Similarity	NPC225854
0.8163	Intermediate Similarity	NPC233961
0.8163	Intermediate Similarity	NPC339621
0.8163	Intermediate Similarity	NPC280399
0.816	Intermediate Similarity	NPC87431
0.816	Intermediate Similarity	NPC96031
0.8153	Intermediate Similarity	NPC203747
0.8153	Intermediate Similarity	NPC254702
0.8153	Intermediate Similarity	NPC139364
0.8153	Intermediate Similarity	NPC194653
0.8153	Intermediate Similarity	NPC80710
0.8148	Intermediate Similarity	NPC209473
0.8148	Intermediate Similarity	NPC179914
0.8144	Intermediate Similarity	NPC103307
0.8141	Intermediate Similarity	NPC316769
0.8141	Intermediate Similarity	NPC12377
0.8137	Intermediate Similarity	NPC470762
0.8137	Intermediate Similarity	NPC472455
0.8137	Intermediate Similarity	NPC317383
0.8137	Intermediate Similarity	NPC474167
0.8133	Intermediate Similarity	NPC208760
0.8129	Intermediate Similarity	NPC142165
0.8129	Intermediate Similarity	NPC105213
0.8125	Intermediate Similarity	NPC155686
0.8125	Intermediate Similarity	NPC469550
0.8125	Intermediate Similarity	NPC124714
0.8125	Intermediate Similarity	NPC303950
0.8121	Intermediate Similarity	NPC300053
0.8121	Intermediate Similarity	NPC108433
0.8121	Intermediate Similarity	NPC472277
0.8121	Intermediate Similarity	NPC475738
0.8117	Intermediate Similarity	NPC273657
0.8117	Intermediate Similarity	NPC312256
0.8117	Intermediate Similarity	NPC185607
0.8117	Intermediate Similarity	NPC106920
0.8113	Intermediate Similarity	NPC95498
0.8113	Intermediate Similarity	NPC262623
0.8113	Intermediate Similarity	NPC246566
0.8113	Intermediate Similarity	NPC476434
0.811	Intermediate Similarity	NPC474034
0.811	Intermediate Similarity	NPC474150
0.811	Intermediate Similarity	NPC474033
0.811	Intermediate Similarity	NPC472635
0.811	Intermediate Similarity	NPC472964
0.811	Intermediate Similarity	NPC206815
0.811	Intermediate Similarity	NPC474162
0.8105	Intermediate Similarity	NPC50823
0.8101	Intermediate Similarity	NPC38545
0.8101	Intermediate Similarity	NPC171916
0.8101	Intermediate Similarity	NPC92722
0.8101	Intermediate Similarity	NPC102003
0.8101	Intermediate Similarity	NPC473091
0.8098	Intermediate Similarity	NPC472961
0.8098	Intermediate Similarity	NPC310399
0.8098	Intermediate Similarity	NPC474936
0.8098	Intermediate Similarity	NPC472962
0.8098	Intermediate Similarity	NPC73422
0.8098	Intermediate Similarity	NPC475784
0.8098	Intermediate Similarity	NPC472902
0.8098	Intermediate Similarity	NPC328102
0.8098	Intermediate Similarity	NPC472624
0.8095	Intermediate Similarity	NPC470685
0.8095	Intermediate Similarity	NPC121333
0.8092	Intermediate Similarity	NPC325625
0.8092	Intermediate Similarity	NPC96194
0.8092	Intermediate Similarity	NPC46947
0.8092	Intermediate Similarity	NPC44573
0.8092	Intermediate Similarity	NPC299855
0.8089	Intermediate Similarity	NPC188074
0.8089	Intermediate Similarity	NPC125449
0.8089	Intermediate Similarity	NPC93034
0.8089	Intermediate Similarity	NPC470511
0.8089	Intermediate Similarity	NPC294972
0.8089	Intermediate Similarity	NPC119660
0.8086	Intermediate Similarity	NPC84935
0.8086	Intermediate Similarity	NPC474055
0.8086	Intermediate Similarity	NPC78103
0.8086	Intermediate Similarity	NPC27337
0.8086	Intermediate Similarity	NPC77679
0.8086	Intermediate Similarity	NPC181960
0.8086	Intermediate Similarity	NPC179732
0.8086	Intermediate Similarity	NPC190020
0.8086	Intermediate Similarity	NPC291508
0.8086	Intermediate Similarity	NPC472598
0.8084	Intermediate Similarity	NPC152477
0.8084	Intermediate Similarity	NPC288813
0.8077	Intermediate Similarity	NPC474799
0.8075	Intermediate Similarity	NPC234255
0.8075	Intermediate Similarity	NPC472280
0.8075	Intermediate Similarity	NPC82592
0.8075	Intermediate Similarity	NPC234485
0.8075	Intermediate Similarity	NPC134287
0.8075	Intermediate Similarity	NPC152951
0.8075	Intermediate Similarity	NPC117992
0.8075	Intermediate Similarity	NPC57674
0.8075	Intermediate Similarity	NPC168247
0.8075	Intermediate Similarity	NPC256925
0.8075	Intermediate Similarity	NPC39184
0.8075	Intermediate Similarity	NPC130589
0.8075	Intermediate Similarity	NPC79998
0.8075	Intermediate Similarity	NPC16082
0.8075	Intermediate Similarity	NPC68727
0.8075	Intermediate Similarity	NPC230149
0.8072	Intermediate Similarity	NPC165460
0.807	Intermediate Similarity	NPC236089
0.8065	Intermediate Similarity	NPC471417
0.8065	Intermediate Similarity	NPC27159
0.8065	Intermediate Similarity	NPC287722

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 NPC476335 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	844
0.2-0.3	1790
0.3-0.4	2671
0.4-0.5	2003
0.5-0.6	1029
0.6-0.7	407
0.7-0.8	86
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
0.8025	Intermediate Similarity	NPD3882	Suspended
0.7988	Intermediate Similarity	NPD5494	Approved
0.795	Intermediate Similarity	NPD1934	Approved
0.7901	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7199	Phase 2
0.7811	Intermediate Similarity	NPD3818	Discontinued
0.7791	Intermediate Similarity	NPD2801	Approved
0.7733	Intermediate Similarity	NPD7685	Pre-registration
0.7733	Intermediate Similarity	NPD3027	Phase 3
0.773	Intermediate Similarity	NPD37	Approved
0.7716	Intermediate Similarity	NPD4380	Phase 2
0.7716	Intermediate Similarity	NPD7028	Phase 2
0.7692	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6166	Phase 2
0.7692	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7473	Discontinued
0.764	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD3817	Phase 2
0.7633	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD4967	Phase 2
0.759	Intermediate Similarity	NPD4966	Approved
0.759	Intermediate Similarity	NPD4965	Approved
0.7576	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6232	Discontinued
0.7557	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD1510	Phase 2
0.7485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7819	Suspended
0.7468	Intermediate Similarity	NPD1240	Approved
0.7457	Intermediate Similarity	NPD7054	Approved
0.7457	Intermediate Similarity	NPD5844	Phase 1
0.7453	Intermediate Similarity	NPD6799	Approved
0.7453	Intermediate Similarity	NPD1511	Approved
0.7452	Intermediate Similarity	NPD2796	Approved
0.744	Intermediate Similarity	NPD7075	Discontinued
0.7427	Intermediate Similarity	NPD3926	Phase 2
0.7419	Intermediate Similarity	NPD230	Phase 1
0.7417	Intermediate Similarity	NPD5647	Approved
0.7414	Intermediate Similarity	NPD7472	Approved
0.7412	Intermediate Similarity	NPD8127	Discontinued
0.7412	Intermediate Similarity	NPD1247	Approved
0.741	Intermediate Similarity	NPD6801	Discontinued
0.7396	Intermediate Similarity	NPD919	Approved
0.7394	Intermediate Similarity	NPD6599	Discontinued
0.7375	Intermediate Similarity	NPD4628	Phase 3
0.7372	Intermediate Similarity	NPD1607	Approved
0.7368	Intermediate Similarity	NPD9494	Approved
0.7362	Intermediate Similarity	NPD1512	Approved
0.7358	Intermediate Similarity	NPD1549	Phase 2
0.7358	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3620	Phase 2
0.7355	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD943	Approved
0.7346	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6190	Approved
0.7321	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2532	Approved
0.7301	Intermediate Similarity	NPD2534	Approved
0.7301	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2533	Approved
0.7299	Intermediate Similarity	NPD7228	Approved
0.7299	Intermediate Similarity	NPD3751	Discontinued
0.7296	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD6797	Phase 2
0.7267	Intermediate Similarity	NPD4110	Phase 3
0.7267	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5761	Phase 2
0.7262	Intermediate Similarity	NPD5760	Phase 2
0.7239	Intermediate Similarity	NPD4357	Discontinued
0.7232	Intermediate Similarity	NPD7251	Discontinued
0.7226	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5353	Approved
0.7211	Intermediate Similarity	NPD5536	Phase 2
0.7205	Intermediate Similarity	NPD2800	Approved
0.7195	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5763	Approved
0.7188	Intermediate Similarity	NPD5762	Approved
0.7175	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3787	Discontinued
0.716	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6653	Approved
0.7152	Intermediate Similarity	NPD6273	Approved
0.7152	Intermediate Similarity	NPD6651	Approved
0.7143	Intermediate Similarity	NPD7411	Suspended
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7135	Intermediate Similarity	NPD7240	Approved
0.7135	Intermediate Similarity	NPD6559	Discontinued
0.7134	Intermediate Similarity	NPD1613	Approved
0.7134	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD8434	Phase 2
0.7126	Intermediate Similarity	NPD5242	Approved
0.7125	Intermediate Similarity	NPD6100	Approved
0.7125	Intermediate Similarity	NPD6099	Approved
0.7118	Intermediate Similarity	NPD5402	Approved
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7089	Intermediate Similarity	NPD5735	Approved
0.7081	Intermediate Similarity	NPD6002	Phase 3
0.7081	Intermediate Similarity	NPD6004	Phase 3
0.7081	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6005	Phase 3
0.7081	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7063	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1465	Phase 2
0.7059	Intermediate Similarity	NPD1876	Approved
0.7055	Intermediate Similarity	NPD5283	Phase 1
0.7019	Intermediate Similarity	NPD2935	Discontinued
0.7018	Intermediate Similarity	NPD5977	Approved
0.7018	Intermediate Similarity	NPD5978	Approved
0.7011	Intermediate Similarity	NPD6959	Discontinued
0.7006	Intermediate Similarity	NPD920	Approved
0.7006	Intermediate Similarity	NPD5403	Approved
0.6993	Remote Similarity	NPD2983	Phase 2
0.6993	Remote Similarity	NPD2982	Phase 2
0.6988	Remote Similarity	NPD5401	Approved
0.6988	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD447	Suspended
0.6968	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1653	Approved
0.6957	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2799	Discontinued
0.6951	Remote Similarity	NPD8166	Discontinued
0.6951	Remote Similarity	NPD3750	Approved
0.6936	Remote Similarity	NPD3749	Approved
0.6928	Remote Similarity	NPD2981	Phase 2
0.6928	Remote Similarity	NPD1608	Approved
0.6923	Remote Similarity	NPD3018	Phase 2
0.6918	Remote Similarity	NPD4140	Approved
0.6914	Remote Similarity	NPD5712	Approved
0.6899	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD2403	Approved
0.6893	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1243	Approved
0.6886	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7768	Phase 2
0.6879	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5124	Phase 1
0.6875	Remote Similarity	NPD3657	Discovery
0.6875	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7229	Phase 3
0.6867	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4624	Approved
0.6852	Remote Similarity	NPD3748	Approved
0.6852	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6765	Approved
0.6851	Remote Similarity	NPD6764	Approved
0.6842	Remote Similarity	NPD6386	Approved
0.6842	Remote Similarity	NPD6385	Approved
0.6831	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1241	Discontinued
0.6818	Remote Similarity	NPD3972	Approved
0.6818	Remote Similarity	NPD9269	Phase 2
0.6815	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD228	Approved
0.6795	Remote Similarity	NPD3094	Phase 2
0.6792	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7497	Discontinued
0.6788	Remote Similarity	NPD2654	Approved
0.678	Remote Similarity	NPD5711	Approved
0.678	Remote Similarity	NPD5710	Approved
0.6776	Remote Similarity	NPD9268	Approved
0.6776	Remote Similarity	NPD1651	Approved
0.6774	Remote Similarity	NPD4749	Approved
0.6772	Remote Similarity	NPD4908	Phase 1
0.6768	Remote Similarity	NPD2344	Approved
0.6766	Remote Similarity	NPD7236	Approved
0.6757	Remote Similarity	NPD8150	Discontinued
0.6753	Remote Similarity	NPD3705	Approved
0.6753	Remote Similarity	NPD3092	Approved
0.6752	Remote Similarity	NPD2798	Approved
0.6744	Remote Similarity	NPD5090	Approved
0.6744	Remote Similarity	NPD5089	Approved
0.6732	Remote Similarity	NPD2932	Approved
0.6732	Remote Similarity	NPD17	Approved
0.6731	Remote Similarity	NPD1283	Approved
0.6728	Remote Similarity	NPD6353	Approved
0.6725	Remote Similarity	NPD7458	Discontinued
0.6722	Remote Similarity	NPD7799	Discontinued
0.6709	Remote Similarity	NPD2861	Phase 2
0.6707	Remote Similarity	NPD2438	Suspended
0.6707	Remote Similarity	NPD1551	Phase 2
0.6703	Remote Similarity	NPD5953	Discontinued
0.6703	Remote Similarity	NPD6784	Approved
0.6703	Remote Similarity	NPD6785	Approved
0.6688	Remote Similarity	NPD6362	Approved
0.6687	Remote Similarity	NPD1652	Phase 2
0.6687	Remote Similarity	NPD3268	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