NPASS Compound

Structure

CID64862 OpenBabel06191715402D 32 36 0 0 1 0 0 0 0 0999 V2000 1.2331 -2.6955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9793 2.0700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9279 -0.2000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1963 -0.8587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6012 -1.5344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0183 1.9031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9072 1.0160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9289 1.2086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4376 -1.0777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9963 -1.0309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2557 -2.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4816 2.0997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3666 0.1311 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1684 0.5637 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4593 -0.8850 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3354 1.5781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4056 0.9109 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.1867 0.2173 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1989 1.0795 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9916 0.1042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9613 -0.7798 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3706 1.1618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1982 -0.4330 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 -0.3348 -3.3657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2585 2.5456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8781 -0.5413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0524 2.0934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6870 -0.7051 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1312 -1.6727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0612 0.6998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1989 2.0766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 21 1 0 0 0 0 10 23 1 0 0 0 0 11 25 2 0 0 0 0 11 30 1 0 0 0 0 12 26 2 0 0 0 0 12 31 1 0 0 0 0 13 18 1 0 0 0 0 13 21 1 1 0 0 0 14 22 1 6 0 0 0 14 23 1 0 0 0 0 15 24 1 1 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 16 32 1 1 0 0 0 17 22 1 0 0 0 0 17 24 1 0 0 0 0 18 23 1 6 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 32 1 1 0 0 0 20 24 1 0 0 0 0 21 5 1 1 0 0 0 21 27 1 0 0 0 0 22 6 1 1 0 0 0 22 28 1 0 0 0 0 23 9 1 6 0 0 0 24 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.24
Volume:	445.927
LogP:	2.093
LogD:	1.113
LogS:	-3.908
# Rotatable Bonds:	4
TPSA:	125.82
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	6.389
Fsp3:	0.917
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.387
MDCK Permeability:	5.147399861016311e-05
Pgp-inhibitor:	0.491
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.393
20% Bioavailability (F20%):	0.411
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	41.04283142089844%
Volume Distribution (VD):	1.181
Pgp-substrate:	39.899696350097656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.375
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.474
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	1.789
Half-life (T1/2):	0.622

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.584
Drug-inuced Liver Injury (DILI):	0.726
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.256
Maximum Recommended Daily Dose:	0.064
Skin Sensitization:	0.077
Carcinogencity:	0.042
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.747

Download Data

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

Natural Product: NPC64862

Natural Product ID:	NPC64862
*Common Name:**	BQXZYRJBFJGDSL-CYAKPIJTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BQXZYRJBFJGDSL-CYAKPIJTSA-N
Standard InCHI:	InChI=1S/C24H36O8/c1-11(25)30-15-9-23-10-21(5,27)13(18(23)31-12(2)26)7-8-14(23)22(6,28)17-16-19(32-16)20(3,4)24(15,17)29/h13-19,27-29H,7-10H2,1-6H3/t13-,14+,15-,16+,17?,18-,19+,21-,22-,23+,24-/m1/s1
SMILES:	CC(=O)O[C@@H]1[C@H]2CC[C@@H]3[C@]1(C[C@@H](OC(=O)C)[C@]1(C([C@]3(C)O)[C@H]3[C@@H](C1(C)C)O3)O)C[C@@]2(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1463056
PubChem CID:	12314926
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002871] Grayanoids

*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
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	flowers	n.a.	n.a.	PMID[15974620]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	Roots	n.a.	n.a.	PMID[26599832]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29272126]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25980	Rhododendron molle	Species	Ericaceae	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
Potency	5

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[491963]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[491963]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	5011.9	nM	PMID[491963]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[491963]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	11220.2	nM	PMID[491963]

☑ 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 NPC64862 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	454
0.1-0.2	4262
0.2-0.3	14983
0.3-0.4	9308
0.4-0.5	6813
0.5-0.6	5401
0.6-0.7	1253
0.7-0.8	184
0.8-0.85	22
0.85-0.9	3
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9383	High Similarity	NPC29342
0.9383	High Similarity	NPC2572
0.9012	High Similarity	NPC66766
0.9012	High Similarity	NPC117137
0.869	High Similarity	NPC69953
0.8605	High Similarity	NPC131365
0.8506	High Similarity	NPC5943
0.8395	Intermediate Similarity	NPC139765
0.8395	Intermediate Similarity	NPC131584
0.8352	Intermediate Similarity	NPC39453
0.8333	Intermediate Similarity	NPC473066
0.8333	Intermediate Similarity	NPC474714
0.8235	Intermediate Similarity	NPC473257
0.8182	Intermediate Similarity	NPC477283
0.8118	Intermediate Similarity	NPC472943
0.8118	Intermediate Similarity	NPC472951
0.8068	Intermediate Similarity	NPC266651
0.8	Intermediate Similarity	NPC476176
0.7978	Intermediate Similarity	NPC215968
0.7978	Intermediate Similarity	NPC155531
0.7931	Intermediate Similarity	NPC477286
0.7931	Intermediate Similarity	NPC286719
0.7907	Intermediate Similarity	NPC186594
0.7889	Intermediate Similarity	NPC472396
0.7882	Intermediate Similarity	NPC471045
0.7849	Intermediate Similarity	NPC256104
0.7849	Intermediate Similarity	NPC182740
0.7849	Intermediate Similarity	NPC211845
0.7849	Intermediate Similarity	NPC122083
0.7841	Intermediate Similarity	NPC111582
0.7841	Intermediate Similarity	NPC477285
0.7831	Intermediate Similarity	NPC472944
0.7831	Intermediate Similarity	NPC472945
0.7816	Intermediate Similarity	NPC470154
0.7816	Intermediate Similarity	NPC190940
0.7802	Intermediate Similarity	NPC56777
0.7802	Intermediate Similarity	NPC201607
0.7802	Intermediate Similarity	NPC22376
0.7789	Intermediate Similarity	NPC156377
0.7766	Intermediate Similarity	NPC470424
0.7765	Intermediate Similarity	NPC476719
0.7765	Intermediate Similarity	NPC171658
0.7738	Intermediate Similarity	NPC186851
0.7732	Intermediate Similarity	NPC470030
0.7727	Intermediate Similarity	NPC477447
0.7727	Intermediate Similarity	NPC477284
0.7727	Intermediate Similarity	NPC60018
0.7727	Intermediate Similarity	NPC202688
0.7727	Intermediate Similarity	NPC470155
0.7727	Intermediate Similarity	NPC216800
0.7727	Intermediate Similarity	NPC477446
0.7727	Intermediate Similarity	NPC475388
0.7727	Intermediate Similarity	NPC154043
0.7677	Intermediate Similarity	NPC139181
0.7677	Intermediate Similarity	NPC97260
0.7677	Intermediate Similarity	NPC476837
0.7674	Intermediate Similarity	NPC43463
0.7653	Intermediate Similarity	NPC476512
0.7653	Intermediate Similarity	NPC472081
0.7653	Intermediate Similarity	NPC108227
0.7647	Intermediate Similarity	NPC136424
0.7614	Intermediate Similarity	NPC216941
0.7614	Intermediate Similarity	NPC470156
0.7609	Intermediate Similarity	NPC470872
0.7604	Intermediate Similarity	NPC252056
0.7604	Intermediate Similarity	NPC116683
0.76	Intermediate Similarity	NPC473701
0.76	Intermediate Similarity	NPC473526
0.7586	Intermediate Similarity	NPC477287
0.7586	Intermediate Similarity	NPC269333
0.7582	Intermediate Similarity	NPC114378
0.7582	Intermediate Similarity	NPC103782
0.7579	Intermediate Similarity	NPC191915
0.7579	Intermediate Similarity	NPC151214
0.7576	Intermediate Similarity	NPC310138
0.7576	Intermediate Similarity	NPC470029
0.7576	Intermediate Similarity	NPC134967
0.7576	Intermediate Similarity	NPC114700
0.7558	Intermediate Similarity	NPC476233
0.7556	Intermediate Similarity	NPC242016
0.7556	Intermediate Similarity	NPC18953
0.7556	Intermediate Similarity	NPC474156
0.7529	Intermediate Similarity	NPC472950
0.7529	Intermediate Similarity	NPC472952
0.7528	Intermediate Similarity	NPC475849
0.7528	Intermediate Similarity	NPC148740
0.7528	Intermediate Similarity	NPC212340
0.7528	Intermediate Similarity	NPC102156
0.75	Intermediate Similarity	NPC16449
0.75	Intermediate Similarity	NPC210658
0.75	Intermediate Similarity	NPC21897
0.75	Intermediate Similarity	NPC161928
0.7475	Intermediate Similarity	NPC476838
0.7475	Intermediate Similarity	NPC476839
0.7475	Intermediate Similarity	NPC475574
0.7474	Intermediate Similarity	NPC475307
0.7473	Intermediate Similarity	NPC235402
0.7471	Intermediate Similarity	NPC252483
0.7471	Intermediate Similarity	NPC191345
0.7449	Intermediate Similarity	NPC292775
0.7444	Intermediate Similarity	NPC259173
0.7444	Intermediate Similarity	NPC474266
0.7442	Intermediate Similarity	NPC470145
0.7423	Intermediate Similarity	NPC238796
0.7423	Intermediate Similarity	NPC237071
0.7423	Intermediate Similarity	NPC296936
0.7423	Intermediate Similarity	NPC203434
0.7419	Intermediate Similarity	NPC128475
0.7416	Intermediate Similarity	NPC119922
0.7416	Intermediate Similarity	NPC116320
0.7416	Intermediate Similarity	NPC73515
0.7416	Intermediate Similarity	NPC211049
0.7412	Intermediate Similarity	NPC475458
0.7396	Intermediate Similarity	NPC175
0.7396	Intermediate Similarity	NPC30687
0.7391	Intermediate Similarity	NPC228593
0.7391	Intermediate Similarity	NPC471240
0.7391	Intermediate Similarity	NPC145245
0.7391	Intermediate Similarity	NPC235196
0.7386	Intermediate Similarity	NPC477282
0.7386	Intermediate Similarity	NPC81074
0.7368	Intermediate Similarity	NPC59006
0.7356	Intermediate Similarity	NPC212453
0.7356	Intermediate Similarity	NPC11907
0.7356	Intermediate Similarity	NPC133596
0.7356	Intermediate Similarity	NPC474574
0.7356	Intermediate Similarity	NPC64081
0.7347	Intermediate Similarity	NPC470591
0.734	Intermediate Similarity	NPC20822
0.734	Intermediate Similarity	NPC228059
0.7333	Intermediate Similarity	NPC470611
0.7333	Intermediate Similarity	NPC164289
0.7333	Intermediate Similarity	NPC242771
0.7333	Intermediate Similarity	NPC100366
0.7333	Intermediate Similarity	NPC311642
0.7326	Intermediate Similarity	NPC317242
0.732	Intermediate Similarity	NPC473064
0.732	Intermediate Similarity	NPC292178
0.732	Intermediate Similarity	NPC473065
0.732	Intermediate Similarity	NPC215570
0.732	Intermediate Similarity	NPC57964
0.732	Intermediate Similarity	NPC94582
0.732	Intermediate Similarity	NPC473067
0.732	Intermediate Similarity	NPC86893
0.7312	Intermediate Similarity	NPC45833
0.7312	Intermediate Similarity	NPC213658
0.7312	Intermediate Similarity	NPC110365
0.7312	Intermediate Similarity	NPC62202
0.7294	Intermediate Similarity	NPC476718
0.7294	Intermediate Similarity	NPC123122
0.7292	Intermediate Similarity	NPC311246
0.7292	Intermediate Similarity	NPC167644
0.729	Intermediate Similarity	NPC470116
0.729	Intermediate Similarity	NPC470115
0.7263	Intermediate Similarity	NPC473542
0.7263	Intermediate Similarity	NPC10274
0.7263	Intermediate Similarity	NPC279329
0.7253	Intermediate Similarity	NPC470070
0.7245	Intermediate Similarity	NPC142264
0.7245	Intermediate Similarity	NPC111834
0.7245	Intermediate Similarity	NPC169270
0.7245	Intermediate Similarity	NPC476510
0.7245	Intermediate Similarity	NPC292718
0.7245	Intermediate Similarity	NPC306797
0.7241	Intermediate Similarity	NPC163597
0.7234	Intermediate Similarity	NPC476379
0.7234	Intermediate Similarity	NPC470009
0.7234	Intermediate Similarity	NPC281004
0.7216	Intermediate Similarity	NPC45959
0.7216	Intermediate Similarity	NPC470423
0.7216	Intermediate Similarity	NPC113500
0.7216	Intermediate Similarity	NPC252253
0.7216	Intermediate Similarity	NPC477495
0.7216	Intermediate Similarity	NPC477224
0.7216	Intermediate Similarity	NPC3538
0.7204	Intermediate Similarity	NPC474448
0.7204	Intermediate Similarity	NPC471410
0.7204	Intermediate Similarity	NPC472745
0.7204	Intermediate Similarity	NPC474008
0.7204	Intermediate Similarity	NPC472272
0.7204	Intermediate Similarity	NPC471411
0.7191	Intermediate Similarity	NPC220379
0.7191	Intermediate Similarity	NPC287452
0.7188	Intermediate Similarity	NPC149966
0.7188	Intermediate Similarity	NPC36372
0.7188	Intermediate Similarity	NPC5632
0.7188	Intermediate Similarity	NPC474065
0.7188	Intermediate Similarity	NPC52756
0.7188	Intermediate Similarity	NPC293609
0.7188	Intermediate Similarity	NPC219516
0.7184	Intermediate Similarity	NPC166079
0.7176	Intermediate Similarity	NPC8004
0.7176	Intermediate Similarity	NPC127283
0.7174	Intermediate Similarity	NPC291310
0.7172	Intermediate Similarity	NPC470028
0.7172	Intermediate Similarity	NPC210157
0.7172	Intermediate Similarity	NPC274793
0.7172	Intermediate Similarity	NPC471241
0.7172	Intermediate Similarity	NPC233649
0.7172	Intermediate Similarity	NPC254121

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 NPC64862 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	530
0.1-0.2	4321
0.2-0.3	3041
0.3-0.4	706
0.4-0.5	368
0.5-0.6	173
0.6-0.7	10
0.7-0.8	1
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
0.73	Intermediate Similarity	NPD1700	Approved
0.6939	Remote Similarity	NPD8171	Discontinued
0.6744	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6928	Phase 2
0.6703	Remote Similarity	NPD6115	Approved
0.6703	Remote Similarity	NPD6118	Approved
0.6703	Remote Similarity	NPD6114	Approved
0.6703	Remote Similarity	NPD6697	Approved
0.6604	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6116	Phase 1
0.6556	Remote Similarity	NPD3702	Approved
0.6526	Remote Similarity	NPD3669	Approved
0.6526	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7327	Approved
0.6491	Remote Similarity	NPD7328	Approved
0.6484	Remote Similarity	NPD6117	Approved
0.6477	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD8033	Approved
0.6435	Remote Similarity	NPD7516	Approved
0.6379	Remote Similarity	NPD8294	Approved
0.6379	Remote Similarity	NPD8377	Approved
0.6325	Remote Similarity	NPD8335	Approved
0.6325	Remote Similarity	NPD8379	Approved
0.6325	Remote Similarity	NPD8378	Approved
0.6325	Remote Similarity	NPD8296	Approved
0.6325	Remote Similarity	NPD8380	Approved
0.6296	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5777	Approved
0.6186	Remote Similarity	NPD7503	Approved
0.6163	Remote Similarity	NPD371	Approved
0.614	Remote Similarity	NPD8133	Approved
0.6126	Remote Similarity	NPD7320	Approved
0.6116	Remote Similarity	NPD7507	Approved
0.6111	Remote Similarity	NPD4787	Phase 1
0.6102	Remote Similarity	NPD6319	Approved
0.6091	Remote Similarity	NPD6008	Approved
0.6087	Remote Similarity	NPD1810	Approved
0.6087	Remote Similarity	NPD1811	Approved
0.6071	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD8297	Approved
0.6019	Remote Similarity	NPD8034	Phase 2
0.6019	Remote Similarity	NPD8035	Phase 2
0.6018	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4632	Approved
0.5981	Remote Similarity	NPD7638	Approved
0.5968	Remote Similarity	NPD7319	Approved
0.5946	Remote Similarity	NPD7128	Approved
0.5946	Remote Similarity	NPD6402	Approved
0.5946	Remote Similarity	NPD6675	Approved
0.5946	Remote Similarity	NPD5739	Approved
0.5935	Remote Similarity	NPD7078	Approved
0.5934	Remote Similarity	NPD2254	Approved
0.5934	Remote Similarity	NPD4244	Approved
0.5934	Remote Similarity	NPD4245	Approved
0.5934	Remote Similarity	NPD2686	Approved
0.5934	Remote Similarity	NPD2687	Approved
0.5929	Remote Similarity	NPD6372	Approved
0.5929	Remote Similarity	NPD6373	Approved
0.5926	Remote Similarity	NPD7640	Approved
0.5926	Remote Similarity	NPD7639	Approved
0.5913	Remote Similarity	NPD6053	Discontinued
0.5902	Remote Similarity	NPD7492	Approved
0.5893	Remote Similarity	NPD6412	Phase 2
0.5872	Remote Similarity	NPD5344	Discontinued
0.587	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6081	Approved
0.587	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6616	Approved
0.5851	Remote Similarity	NPD3703	Phase 2
0.5849	Remote Similarity	NPD7991	Discontinued
0.5841	Remote Similarity	NPD6899	Approved
0.5841	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6881	Approved
0.5833	Remote Similarity	NPD6059	Approved
0.5833	Remote Similarity	NPD6054	Approved
0.5833	Remote Similarity	NPD4802	Phase 2
0.5833	Remote Similarity	NPD4238	Approved
0.5826	Remote Similarity	NPD6650	Approved
0.5826	Remote Similarity	NPD6649	Approved
0.5824	Remote Similarity	NPD3698	Phase 2
0.582	Remote Similarity	NPD7604	Phase 2
0.5818	Remote Similarity	NPD7632	Discontinued
0.5816	Remote Similarity	NPD1780	Approved
0.5816	Remote Similarity	NPD1779	Approved
0.5806	Remote Similarity	NPD8293	Discontinued
0.5789	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD7524	Approved
0.5776	Remote Similarity	NPD6882	Approved
0.5763	Remote Similarity	NPD6940	Discontinued
0.576	Remote Similarity	NPD7736	Approved
0.5752	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD5697	Approved
0.5752	Remote Similarity	NPD5701	Approved
0.5743	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6084	Phase 2
0.5741	Remote Similarity	NPD6083	Phase 2
0.5739	Remote Similarity	NPD6883	Approved
0.5739	Remote Similarity	NPD7290	Approved
0.5739	Remote Similarity	NPD7102	Approved
0.5739	Remote Similarity	NPD6371	Approved
0.5738	Remote Similarity	NPD6370	Approved
0.573	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5360	Phase 3
0.5714	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD6009	Approved
0.5714	Remote Similarity	NPD7525	Registered
0.5714	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD5695	Phase 3
0.5701	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD3198	Approved
0.569	Remote Similarity	NPD6869	Approved
0.569	Remote Similarity	NPD8130	Phase 1
0.569	Remote Similarity	NPD6847	Approved
0.569	Remote Similarity	NPD6617	Approved
0.5673	Remote Similarity	NPD6051	Approved
0.5667	Remote Similarity	NPD4224	Phase 2
0.566	Remote Similarity	NPD6399	Phase 3
0.5656	Remote Similarity	NPD5983	Phase 2
0.5656	Remote Similarity	NPD6016	Approved
0.5656	Remote Similarity	NPD6015	Approved
0.5652	Remote Similarity	NPD6012	Approved
0.5652	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6013	Approved
0.5652	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6014	Approved
0.5644	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6648	Approved
0.5631	Remote Similarity	NPD4250	Approved
0.5631	Remote Similarity	NPD4251	Approved
0.561	Remote Similarity	NPD5988	Approved
0.56	Remote Similarity	NPD6336	Discontinued

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