NPASS Compound

Structure

NPC62572 OpenBabel07101718192D 34 39 0 0 1 0 0 0 0 0999 V2000 -2.4178 -1.4416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4445 -1.3979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3493 -1.9486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8621 -1.1048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5313 -0.4871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5313 -3.4100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6875 -2.9228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6875 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3512 -0.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2259 0.4459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5313 -1.4614 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 -1.4614 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3750 -2.9228 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8438 -0.4871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6875 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6141 -0.3011 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6141 1.2753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9690 -0.5768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3750 -1.9486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6875 -1.9486 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 -0.4871 0.0000 C 0 0 1 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 -1.6875 0.9743 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6875 -1.9486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2188 -3.4100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9152 2.2019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1868 0.4871 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 29 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 21 1 0 0 0 0 17 31 2 0 0 0 0 18 26 1 0 0 0 0 18 27 1 1 0 0 0 19 27 1 1 0 0 0 19 28 1 0 0 0 0 20 26 1 0 0 0 0 20 32 1 1 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 23 1 0 0 0 0 22 30 1 6 0 0 0 23 25 1 0 0 0 0 23 34 1 6 0 0 0 24 30 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 6 0 0 0 29 7 1 6 0 0 0 30 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	505.985
LogP:	5.001
LogD:	5.126
LogS:	-5.111
# Rotatable Bonds:	0
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.445
Synthetic Accessibility Score:	5.753
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.201
MDCK Permeability:	3.0954997782828286e-05
Pgp-inhibitor:	0.724
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.577
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.287
Plasma Protein Binding (PPB):	94.4055404663086%
Volume Distribution (VD):	0.857
Pgp-substrate:	3.241030216217041%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.291
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.173
CYP2C9-substrate:	0.428
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.77
CYP3A4-inhibitor:	0.373
CYP3A4-substrate:	0.417

ADMET: Excretion

Clearance (CL):	5.442
Half-life (T1/2):	0.237

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.212
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.788
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.157
Carcinogencity:	0.011
Eye Corrosion:	0.129
Eye Irritation:	0.482
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC62572

Natural Product ID:	NPC62572
*Common Name:**	SCCTYGDZBVYNDP-QYEHROKOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SCCTYGDZBVYNDP-QYEHROKOSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-25(2)12-14-30-15-13-29(7)21(22(30)23(25)34-24(30)33)17(31)16-19-27(5)10-9-20(32)26(3,4)18(27)8-11-28(19,29)6/h18-23,32H,8-16H2,1-7H3/t18-,19+,20-,21-,22+,23+,27-,28+,29+,30-/m0/s1
SMILES:	O=C1C[C@@H]2[C@@]3(C)CC[C@@H](C([C@@H]3CC[C@]2([C@]2([C@@H]1[C@@H]1[C@H]3OC(=O)[C@]1(CC2)CCC3(C)C)C)C)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499859
PubChem CID:	11691319
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	resin	n.a.	n.a.	PMID[16724846]
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12830	Styrax tonkinensis	Species	Styracaceae	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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IG50	=	51.2	uM	PMID[543440]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	<	10.0	%	PMID[543440]

☑ 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 NPC62572 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	397
0.1-0.2	3263
0.2-0.3	11087
0.3-0.4	12888
0.4-0.5	6045
0.5-0.6	4540
0.6-0.7	3454
0.7-0.8	911
0.8-0.85	77
0.85-0.9	30
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.925	High Similarity	NPC280781
0.925	High Similarity	NPC48756
0.9186	High Similarity	NPC472148
0.9186	High Similarity	NPC472147
0.8902	High Similarity	NPC61107
0.8902	High Similarity	NPC289486
0.8902	High Similarity	NPC30583
0.8875	High Similarity	NPC31031
0.8875	High Similarity	NPC472608
0.8875	High Similarity	NPC243594
0.878	High Similarity	NPC271572
0.878	High Similarity	NPC474870
0.878	High Similarity	NPC50658
0.8765	High Similarity	NPC73013
0.8736	High Similarity	NPC472146
0.8736	High Similarity	NPC185529
0.869	High Similarity	NPC473299
0.869	High Similarity	NPC25037
0.869	High Similarity	NPC105895
0.869	High Similarity	NPC34984
0.8642	High Similarity	NPC26029
0.8625	High Similarity	NPC108840
0.8621	High Similarity	NPC471459
0.8621	High Similarity	NPC67653
0.8608	High Similarity	NPC159325
0.8608	High Similarity	NPC168511
0.8554	High Similarity	NPC476071
0.8488	Intermediate Similarity	NPC120395
0.8488	Intermediate Similarity	NPC248216
0.8481	Intermediate Similarity	NPC282905
0.8481	Intermediate Similarity	NPC477229
0.8481	Intermediate Similarity	NPC68426
0.8471	Intermediate Similarity	NPC237938
0.8471	Intermediate Similarity	NPC219535
0.8462	Intermediate Similarity	NPC163685
0.8434	Intermediate Similarity	NPC261616
0.8352	Intermediate Similarity	NPC82633
0.8333	Intermediate Similarity	NPC58631
0.8315	Intermediate Similarity	NPC50443
0.8315	Intermediate Similarity	NPC18536
0.8313	Intermediate Similarity	NPC320144
0.8295	Intermediate Similarity	NPC131104
0.8295	Intermediate Similarity	NPC473319
0.8295	Intermediate Similarity	NPC236459
0.8295	Intermediate Similarity	NPC3032
0.8293	Intermediate Similarity	NPC298168
0.8293	Intermediate Similarity	NPC143133
0.8276	Intermediate Similarity	NPC83242
0.8272	Intermediate Similarity	NPC267753
0.8272	Intermediate Similarity	NPC179858
0.8261	Intermediate Similarity	NPC235109
0.825	Intermediate Similarity	NPC475230
0.8242	Intermediate Similarity	NPC247877
0.8242	Intermediate Similarity	NPC309127
0.8193	Intermediate Similarity	NPC185465
0.8172	Intermediate Similarity	NPC472145
0.8171	Intermediate Similarity	NPC475742
0.8171	Intermediate Similarity	NPC471046
0.8171	Intermediate Similarity	NPC5767
0.8171	Intermediate Similarity	NPC4209
0.8148	Intermediate Similarity	NPC130011
0.8125	Intermediate Similarity	NPC290058
0.8111	Intermediate Similarity	NPC475211
0.8111	Intermediate Similarity	NPC88337
0.8095	Intermediate Similarity	NPC80891
0.8095	Intermediate Similarity	NPC201276
0.8095	Intermediate Similarity	NPC472310
0.8085	Intermediate Similarity	NPC472144
0.8072	Intermediate Similarity	NPC307865
0.8072	Intermediate Similarity	NPC207010
0.8072	Intermediate Similarity	NPC112463
0.8072	Intermediate Similarity	NPC23884
0.8072	Intermediate Similarity	NPC317913
0.8072	Intermediate Similarity	NPC221420
0.8049	Intermediate Similarity	NPC97534
0.8049	Intermediate Similarity	NPC212733
0.8049	Intermediate Similarity	NPC472311
0.8049	Intermediate Similarity	NPC174964
0.8049	Intermediate Similarity	NPC195155
0.8046	Intermediate Similarity	NPC471044
0.8046	Intermediate Similarity	NPC473336
0.8046	Intermediate Similarity	NPC477434
0.7978	Intermediate Similarity	NPC470920
0.7976	Intermediate Similarity	NPC171426
0.7976	Intermediate Similarity	NPC324700
0.7976	Intermediate Similarity	NPC80089
0.7976	Intermediate Similarity	NPC34046
0.7976	Intermediate Similarity	NPC224802
0.7975	Intermediate Similarity	NPC2568
0.7975	Intermediate Similarity	NPC469724
0.7975	Intermediate Similarity	NPC103647
0.7975	Intermediate Similarity	NPC180777
0.7975	Intermediate Similarity	NPC31187
0.7975	Intermediate Similarity	NPC260319
0.7975	Intermediate Similarity	NPC281203
0.7975	Intermediate Similarity	NPC100917
0.7955	Intermediate Similarity	NPC477445
0.7952	Intermediate Similarity	NPC472487
0.7952	Intermediate Similarity	NPC472486
0.7935	Intermediate Similarity	NPC474436
0.7935	Intermediate Similarity	NPC63118
0.7935	Intermediate Similarity	NPC49776
0.7927	Intermediate Similarity	NPC133922
0.7927	Intermediate Similarity	NPC280026
0.7927	Intermediate Similarity	NPC167702
0.7901	Intermediate Similarity	NPC89310
0.7889	Intermediate Similarity	NPC474719
0.7872	Intermediate Similarity	NPC223169
0.7865	Intermediate Similarity	NPC187545
0.7849	Intermediate Similarity	NPC303863
0.7841	Intermediate Similarity	NPC181871
0.7841	Intermediate Similarity	NPC474996
0.7841	Intermediate Similarity	NPC9060
0.7841	Intermediate Similarity	NPC319909
0.7831	Intermediate Similarity	NPC125767
0.7831	Intermediate Similarity	NPC21220
0.7826	Intermediate Similarity	NPC475878
0.7805	Intermediate Similarity	NPC109510
0.7805	Intermediate Similarity	NPC81759
0.7805	Intermediate Similarity	NPC232112
0.78	Intermediate Similarity	NPC316930
0.7789	Intermediate Similarity	NPC470632
0.7778	Intermediate Similarity	NPC33768
0.7778	Intermediate Similarity	NPC252714
0.7753	Intermediate Similarity	NPC474572
0.775	Intermediate Similarity	NPC470956
0.7742	Intermediate Similarity	NPC224060
0.7742	Intermediate Similarity	NPC294263
0.7742	Intermediate Similarity	NPC476189
0.7742	Intermediate Similarity	NPC244356
0.7727	Intermediate Similarity	NPC15091
0.7727	Intermediate Similarity	NPC269684
0.7723	Intermediate Similarity	NPC320475
0.7723	Intermediate Similarity	NPC321661
0.7717	Intermediate Similarity	NPC291028
0.7717	Intermediate Similarity	NPC470114
0.7717	Intermediate Similarity	NPC77756
0.7711	Intermediate Similarity	NPC55508
0.7711	Intermediate Similarity	NPC74639
0.7708	Intermediate Similarity	NPC474724
0.7708	Intermediate Similarity	NPC164349
0.7701	Intermediate Similarity	NPC475743
0.7701	Intermediate Similarity	NPC12933
0.7692	Intermediate Similarity	NPC4309
0.7692	Intermediate Similarity	NPC90676
0.7683	Intermediate Similarity	NPC469940
0.7683	Intermediate Similarity	NPC58057
0.7683	Intermediate Similarity	NPC156277
0.7683	Intermediate Similarity	NPC320549
0.7683	Intermediate Similarity	NPC247195
0.7683	Intermediate Similarity	NPC151018
0.7683	Intermediate Similarity	NPC472309
0.7677	Intermediate Similarity	NPC327093
0.7674	Intermediate Similarity	NPC220379
0.7667	Intermediate Similarity	NPC12774
0.7667	Intermediate Similarity	NPC2783
0.7667	Intermediate Similarity	NPC92139
0.7667	Intermediate Similarity	NPC80700
0.7654	Intermediate Similarity	NPC131892
0.7654	Intermediate Similarity	NPC213178
0.7654	Intermediate Similarity	NPC295788
0.7654	Intermediate Similarity	NPC327728
0.7654	Intermediate Similarity	NPC178541
0.7654	Intermediate Similarity	NPC6120
0.7647	Intermediate Similarity	NPC477918
0.7634	Intermediate Similarity	NPC105189
0.7634	Intermediate Similarity	NPC52756
0.7634	Intermediate Similarity	NPC160506
0.7629	Intermediate Similarity	NPC80417
0.7625	Intermediate Similarity	NPC472984
0.7625	Intermediate Similarity	NPC41542
0.7619	Intermediate Similarity	NPC159789
0.7619	Intermediate Similarity	NPC273366
0.7614	Intermediate Similarity	NPC208912
0.7614	Intermediate Similarity	NPC328007
0.7614	Intermediate Similarity	NPC268040
0.7614	Intermediate Similarity	NPC13494
0.7614	Intermediate Similarity	NPC121121
0.7614	Intermediate Similarity	NPC2096
0.7609	Intermediate Similarity	NPC477443
0.7609	Intermediate Similarity	NPC61688
0.7609	Intermediate Similarity	NPC30522
0.7609	Intermediate Similarity	NPC200580
0.7609	Intermediate Similarity	NPC477440
0.7604	Intermediate Similarity	NPC74466
0.7604	Intermediate Similarity	NPC470425
0.7595	Intermediate Similarity	NPC469791
0.759	Intermediate Similarity	NPC253805
0.759	Intermediate Similarity	NPC474755
0.7586	Intermediate Similarity	NPC125366
0.7586	Intermediate Similarity	NPC477851
0.7582	Intermediate Similarity	NPC264005
0.7582	Intermediate Similarity	NPC269360
0.7579	Intermediate Similarity	NPC287354
0.7579	Intermediate Similarity	NPC98639
0.7579	Intermediate Similarity	NPC62407
0.7561	Intermediate Similarity	NPC477929
0.7561	Intermediate Similarity	NPC108131
0.7558	Intermediate Similarity	NPC329117
0.7556	Intermediate Similarity	NPC294438

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 NPC62572 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	419
0.1-0.2	3439
0.2-0.3	3580
0.3-0.4	1090
0.4-0.5	290
0.5-0.6	204
0.6-0.7	99
0.7-0.8	27
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8171	Intermediate Similarity	NPD6117	Approved
0.8072	Intermediate Similarity	NPD6116	Phase 1
0.7976	Intermediate Similarity	NPD6114	Approved
0.7976	Intermediate Similarity	NPD6115	Approved
0.7976	Intermediate Similarity	NPD6697	Approved
0.7976	Intermediate Similarity	NPD6118	Approved
0.7927	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6081	Approved
0.7683	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD8034	Phase 2
0.7634	Intermediate Similarity	NPD8035	Phase 2
0.7619	Intermediate Similarity	NPD3703	Phase 2
0.7556	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7748	Approved
0.747	Intermediate Similarity	NPD5777	Approved
0.7447	Intermediate Similarity	NPD7515	Phase 2
0.7423	Intermediate Similarity	NPD7902	Approved
0.7349	Intermediate Similarity	NPD4245	Approved
0.7349	Intermediate Similarity	NPD4244	Approved
0.7284	Intermediate Similarity	NPD4224	Phase 2
0.7229	Intermediate Similarity	NPD3698	Phase 2
0.7209	Intermediate Similarity	NPD3702	Approved
0.7143	Intermediate Similarity	NPD4789	Approved
0.7113	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7900	Approved
0.7108	Intermediate Similarity	NPD5360	Phase 3
0.7108	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3671	Phase 1
0.6951	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6399	Phase 3
0.6827	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4758	Discontinued
0.6628	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5739	Approved
0.6604	Remote Similarity	NPD6675	Approved
0.6604	Remote Similarity	NPD7128	Approved
0.6604	Remote Similarity	NPD6402	Approved
0.6593	Remote Similarity	NPD5364	Discontinued
0.6574	Remote Similarity	NPD6372	Approved
0.6574	Remote Similarity	NPD6373	Approved
0.6574	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3618	Phase 1
0.6531	Remote Similarity	NPD5328	Approved
0.6505	Remote Similarity	NPD7638	Approved
0.6481	Remote Similarity	NPD7320	Approved
0.6481	Remote Similarity	NPD6881	Approved
0.6481	Remote Similarity	NPD6899	Approved
0.6481	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.646	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6649	Approved
0.6455	Remote Similarity	NPD6650	Approved
0.6452	Remote Similarity	NPD6928	Phase 2
0.6449	Remote Similarity	NPD6920	Discontinued
0.6442	Remote Similarity	NPD7640	Approved
0.6442	Remote Similarity	NPD7639	Approved
0.6442	Remote Similarity	NPD8418	Phase 2
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6079	Approved
0.6389	Remote Similarity	NPD5701	Approved
0.6389	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD7102	Approved
0.6364	Remote Similarity	NPD6883	Approved
0.6364	Remote Similarity	NPD7290	Approved
0.6354	Remote Similarity	NPD4786	Approved
0.6346	Remote Similarity	NPD5696	Approved
0.6344	Remote Similarity	NPD7645	Phase 2
0.633	Remote Similarity	NPD6011	Approved
0.6329	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7632	Discontinued
0.6316	Remote Similarity	NPD3667	Approved
0.6311	Remote Similarity	NPD7614	Phase 1
0.6311	Remote Similarity	NPD4697	Phase 3
0.6306	Remote Similarity	NPD8130	Phase 1
0.6306	Remote Similarity	NPD6617	Approved
0.6306	Remote Similarity	NPD6847	Approved
0.6306	Remote Similarity	NPD6869	Approved
0.6306	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6012	Approved
0.6273	Remote Similarity	NPD6014	Approved
0.6273	Remote Similarity	NPD6013	Approved
0.6271	Remote Similarity	NPD8328	Phase 3
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD4788	Approved
0.6235	Remote Similarity	NPD7909	Approved
0.6224	Remote Similarity	NPD7334	Approved
0.6224	Remote Similarity	NPD6684	Approved
0.6224	Remote Similarity	NPD6409	Approved
0.6224	Remote Similarity	NPD7146	Approved
0.6224	Remote Similarity	NPD7521	Approved
0.6224	Remote Similarity	NPD5330	Approved
0.6214	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD8133	Approved
0.618	Remote Similarity	NPD4787	Phase 1
0.6174	Remote Similarity	NPD7115	Discovery
0.6162	Remote Similarity	NPD3573	Approved
0.6154	Remote Similarity	NPD5222	Approved
0.6154	Remote Similarity	NPD5221	Approved
0.6154	Remote Similarity	NPD7732	Phase 3
0.6154	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6008	Approved
0.6145	Remote Similarity	NPD3198	Approved
0.6136	Remote Similarity	NPD229	Approved
0.6125	Remote Similarity	NPD615	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5737	Approved
0.61	Remote Similarity	NPD6672	Approved
0.61	Remote Similarity	NPD6903	Approved
0.6095	Remote Similarity	NPD5173	Approved
0.6095	Remote Similarity	NPD4755	Approved
0.6087	Remote Similarity	NPD6868	Approved
0.6078	Remote Similarity	NPD6411	Approved
0.6075	Remote Similarity	NPD1700	Approved
0.6064	Remote Similarity	NPD4802	Phase 2
0.6064	Remote Similarity	NPD4238	Approved
0.6042	Remote Similarity	NPD1779	Approved
0.6042	Remote Similarity	NPD1780	Approved
0.6038	Remote Similarity	NPD4225	Approved
0.602	Remote Similarity	NPD3665	Phase 1
0.602	Remote Similarity	NPD3666	Approved
0.602	Remote Similarity	NPD3133	Approved
0.6019	Remote Similarity	NPD4202	Approved
0.6019	Remote Similarity	NPD8171	Discontinued
0.5983	Remote Similarity	NPD6335	Approved
0.5982	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5285	Approved
0.5981	Remote Similarity	NPD5286	Approved
0.5981	Remote Similarity	NPD4700	Approved
0.5981	Remote Similarity	NPD4696	Approved
0.5966	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.596	Remote Similarity	NPD1694	Approved
0.5948	Remote Similarity	NPD6274	Approved
0.5948	Remote Similarity	NPD6940	Discontinued
0.5938	Remote Similarity	NPD7525	Registered
0.5935	Remote Similarity	NPD7736	Approved
0.5932	Remote Similarity	NPD7100	Approved
0.5932	Remote Similarity	NPD7101	Approved
0.5929	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5223	Approved
0.5918	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD3669	Approved
0.5913	Remote Similarity	NPD4632	Approved
0.5913	Remote Similarity	NPD8298	Phase 2
0.5905	Remote Similarity	NPD5210	Approved
0.5905	Remote Similarity	NPD4629	Approved
0.5905	Remote Similarity	NPD5695	Phase 3
0.59	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6317	Approved
0.5893	Remote Similarity	NPD6415	Discontinued
0.5882	Remote Similarity	NPD6101	Approved
0.5882	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5225	Approved
0.5872	Remote Similarity	NPD4633	Approved
0.5872	Remote Similarity	NPD5211	Phase 2
0.5872	Remote Similarity	NPD5226	Approved
0.5872	Remote Similarity	NPD5224	Approved
0.5859	Remote Similarity	NPD3668	Phase 3
0.5847	Remote Similarity	NPD6313	Approved
0.5847	Remote Similarity	NPD6314	Approved
0.5833	Remote Similarity	NPD6921	Approved
0.5833	Remote Similarity	NPD6909	Approved
0.5833	Remote Similarity	NPD6908	Approved
0.582	Remote Similarity	NPD7492	Approved
0.5818	Remote Similarity	NPD5174	Approved
0.5818	Remote Similarity	NPD4754	Approved
0.5818	Remote Similarity	NPD5175	Approved
0.581	Remote Similarity	NPD6001	Approved
0.5804	Remote Similarity	NPD6412	Phase 2
0.5804	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD6616	Approved
0.5772	Remote Similarity	NPD7507	Approved
0.5766	Remote Similarity	NPD5141	Approved
0.5763	Remote Similarity	NPD6009	Approved
0.575	Remote Similarity	NPD6059	Approved
0.575	Remote Similarity	NPD6054	Approved
0.575	Remote Similarity	NPD6319	Approved
0.5743	Remote Similarity	NPD6098	Approved
0.5738	Remote Similarity	NPD7604	Phase 2
0.5729	Remote Similarity	NPD3617	Approved
0.5728	Remote Similarity	NPD6673	Approved
0.5728	Remote Similarity	NPD6080	Approved
0.5728	Remote Similarity	NPD4753	Phase 2
0.5728	Remote Similarity	NPD6904	Approved
0.5726	Remote Similarity	NPD8293	Discontinued
0.5726	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD3725	Approved
0.5714	Remote Similarity	NPD3726	Approved
0.5714	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD4768	Approved
0.5702	Remote Similarity	NPD5983	Phase 2
0.5664	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD6435	Approved
0.5656	Remote Similarity	NPD6370	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