NPASS Compound

Structure

NPC121566 OpenBabel07101719132D 36 40 0 0 1 0 0 0 0 0999 V2000 4.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8023 2.3406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2091 1.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9941 -2.6844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3305 0.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 -0.0388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1965 0.1303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1100 0.5371 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9941 -0.9523 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2146 1.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 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 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9191 -0.0507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4055 2.1194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4941 -1.8184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9886 -0.8478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 6 30 1 0 0 0 0 8 35 1 0 0 0 0 9 10 1 0 0 0 0 9 21 2 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 29 1 0 0 0 0 15 31 1 0 0 0 0 16 30 1 0 0 0 0 17 22 1 0 0 0 0 18 17 1 1 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 30 1 1 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 31 1 0 0 0 0 22 25 1 1 0 0 0 22 36 1 0 0 0 0 23 27 1 0 0 0 0 23 29 1 1 0 0 0 24 27 1 0 0 0 0 24 32 2 0 0 0 0 25 28 1 0 0 0 0 25 33 1 6 0 0 0 26 35 1 6 0 0 0 26 36 1 0 0 0 0 28 34 1 0 0 0 0 29 5 1 1 0 0 0 30 31 1 6 0 0 0 31 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.37
Volume:	540.628
LogP:	5.122
LogD:	4.448
LogS:	-4.613
# Rotatable Bonds:	4
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.485
Synthetic Accessibility Score:	5.118
Fsp3:	0.903
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-4.924
MDCK Permeability:	1.1544245353434235e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.84
30% Bioavailability (F30%):	0.942

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.116
Plasma Protein Binding (PPB):	91.16651153564453%
Volume Distribution (VD):	1.595
Pgp-substrate:	3.842668294906616%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.648
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.125
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.65
CYP3A4-substrate:	0.712

ADMET: Excretion

Clearance (CL):	7.404
Half-life (T1/2):	0.223

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.289
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.72
Maximum Recommended Daily Dose:	0.818
Skin Sensitization:	0.066
Carcinogencity:	0.093
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC121566

Natural Product ID:	NPC121566
*Common Name:**	21Alpha-Methylmelianodiol
IUPAC Name:	(5R,9R,10R,13S,14S,17R)-17-[(2R,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:	21Alpha-Methylmelianodiol
Standard InCHIKey:	NYUZBOBAGWNMHW-KMILWBBFSA-N
Standard InCHI:	InChI=1S/C31H50O5/c1-27(2)23-10-9-21-20(29(23,5)14-13-24(27)32)12-16-30(6)19(11-15-31(21,30)7)18-17-22(36-26(18)35-8)25(33)28(3,4)34/h9,18-20,22-23,25-26,33-34H,10-17H2,1-8H3/t18-,19+,20-,22+,23-,25-,26+,29+,30-,31+/m0/s1
SMILES:	CC1(C)[C@@H]2CC=C3[C@H](CC[C@@]4(C)[C@H](CC[C@]34C)[C@@H]3C[C@H]([C@@H](C(C)(C)O)O)O[C@H]3OC)[C@@]2(C)CCC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668619
PubChem CID:	53324041
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
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943621]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Yunnan, China	2007-May	PMID[21288727]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32208696]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	29400.0	nM	PMID[543177]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	54600.0	nM	PMID[543177]

☑ 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 NPC121566 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	208
0.1-0.2	1260
0.2-0.3	5070
0.3-0.4	12053
0.4-0.5	9241
0.5-0.6	5936
0.6-0.7	6144
0.7-0.8	2543
0.8-0.85	194
0.85-0.9	36
0.9-0.95	6
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC100955
0.9897	High Similarity	NPC95243
0.9897	High Similarity	NPC63023
0.9314	High Similarity	NPC101450
0.9126	High Similarity	NPC475317
0.9126	High Similarity	NPC154856
0.9126	High Similarity	NPC52241
0.9048	High Similarity	NPC477944
0.9029	High Similarity	NPC246205
0.899	High Similarity	NPC167974
0.8952	High Similarity	NPC210420
0.8952	High Similarity	NPC474265
0.8952	High Similarity	NPC130427
0.8942	High Similarity	NPC470065
0.8932	High Similarity	NPC295389
0.8932	High Similarity	NPC258323
0.8922	High Similarity	NPC210178
0.8922	High Similarity	NPC162033
0.8889	High Similarity	NPC216260
0.8889	High Similarity	NPC5358
0.8868	High Similarity	NPC178981
0.8824	High Similarity	NPC31430
0.8824	High Similarity	NPC223741
0.8824	High Similarity	NPC85593
0.8785	High Similarity	NPC473882
0.8785	High Similarity	NPC477580
0.8785	High Similarity	NPC474557
0.875	High Similarity	NPC473288
0.8704	High Similarity	NPC279638
0.8692	High Similarity	NPC471173
0.8692	High Similarity	NPC471627
0.8692	High Similarity	NPC260665
0.8679	High Similarity	NPC263827
0.8679	High Similarity	NPC250481
0.8679	High Similarity	NPC285410
0.8679	High Similarity	NPC269466
0.8673	High Similarity	NPC174051
0.8673	High Similarity	NPC67831
0.8667	High Similarity	NPC118225
0.8636	High Similarity	NPC161738
0.8614	High Similarity	NPC324598
0.8611	High Similarity	NPC74727
0.8586	High Similarity	NPC108141
0.8585	High Similarity	NPC129340
0.8585	High Similarity	NPC27551
0.8585	High Similarity	NPC114961
0.8571	High Similarity	NPC224414
0.8545	High Similarity	NPC475632
0.8545	High Similarity	NPC86020
0.8542	High Similarity	NPC470417
0.8532	High Similarity	NPC302471
0.8519	High Similarity	NPC73455
0.8519	High Similarity	NPC200944
0.8515	High Similarity	NPC56071
0.8515	High Similarity	NPC70733
0.8491	Intermediate Similarity	NPC265655
0.8482	Intermediate Similarity	NPC182900
0.8482	Intermediate Similarity	NPC476544
0.8482	Intermediate Similarity	NPC476672
0.8482	Intermediate Similarity	NPC476543
0.8482	Intermediate Similarity	NPC249553
0.8482	Intermediate Similarity	NPC476545
0.8476	Intermediate Similarity	NPC59530
0.8476	Intermediate Similarity	NPC293512
0.8469	Intermediate Similarity	NPC262870
0.8468	Intermediate Similarity	NPC477071
0.8462	Intermediate Similarity	NPC471293
0.8454	Intermediate Similarity	NPC473058
0.8447	Intermediate Similarity	NPC154452
0.8447	Intermediate Similarity	NPC94919
0.844	Intermediate Similarity	NPC471398
0.844	Intermediate Similarity	NPC165439
0.8438	Intermediate Similarity	NPC251808
0.8438	Intermediate Similarity	NPC90652
0.8438	Intermediate Similarity	NPC474174
0.8421	Intermediate Similarity	NPC476674
0.8416	Intermediate Similarity	NPC243728
0.8416	Intermediate Similarity	NPC473890
0.8411	Intermediate Similarity	NPC106760
0.8411	Intermediate Similarity	NPC127153
0.8407	Intermediate Similarity	NPC15918
0.8407	Intermediate Similarity	NPC94072
0.8407	Intermediate Similarity	NPC305771
0.8407	Intermediate Similarity	NPC169816
0.84	Intermediate Similarity	NPC230347
0.84	Intermediate Similarity	NPC286612
0.84	Intermediate Similarity	NPC275310
0.8396	Intermediate Similarity	NPC195708
0.8393	Intermediate Similarity	NPC475187
0.8393	Intermediate Similarity	NPC471406
0.8381	Intermediate Similarity	NPC96377
0.8381	Intermediate Similarity	NPC470309
0.8381	Intermediate Similarity	NPC26798
0.8378	Intermediate Similarity	NPC45475
0.8367	Intermediate Similarity	NPC159876
0.8365	Intermediate Similarity	NPC213190
0.8364	Intermediate Similarity	NPC244127
0.835	Intermediate Similarity	NPC121072
0.835	Intermediate Similarity	NPC21064
0.8349	Intermediate Similarity	NPC251309
0.8333	Intermediate Similarity	NPC292196
0.8333	Intermediate Similarity	NPC41129
0.8333	Intermediate Similarity	NPC158088
0.8333	Intermediate Similarity	NPC272242
0.8333	Intermediate Similarity	NPC309493
0.8318	Intermediate Similarity	NPC477070
0.8318	Intermediate Similarity	NPC8431
0.8318	Intermediate Similarity	NPC477069
0.8317	Intermediate Similarity	NPC207617
0.8304	Intermediate Similarity	NPC474179
0.8304	Intermediate Similarity	NPC475834
0.8304	Intermediate Similarity	NPC161065
0.8302	Intermediate Similarity	NPC226642
0.8286	Intermediate Similarity	NPC470059
0.8286	Intermediate Similarity	NPC255309
0.8286	Intermediate Similarity	NPC470057
0.8286	Intermediate Similarity	NPC470062
0.8286	Intermediate Similarity	NPC470064
0.8286	Intermediate Similarity	NPC470060
0.8286	Intermediate Similarity	NPC470043
0.8286	Intermediate Similarity	NPC470058
0.8286	Intermediate Similarity	NPC470061
0.8273	Intermediate Similarity	NPC116024
0.8273	Intermediate Similarity	NPC220293
0.8269	Intermediate Similarity	NPC473928
0.8261	Intermediate Similarity	NPC190846
0.8261	Intermediate Similarity	NPC473505
0.8261	Intermediate Similarity	NPC277191
0.8257	Intermediate Similarity	NPC233003
0.8252	Intermediate Similarity	NPC282669
0.8252	Intermediate Similarity	NPC469942
0.8246	Intermediate Similarity	NPC475431
0.8246	Intermediate Similarity	NPC156789
0.8246	Intermediate Similarity	NPC28532
0.8235	Intermediate Similarity	NPC187159
0.823	Intermediate Similarity	NPC241192
0.823	Intermediate Similarity	NPC129393
0.8214	Intermediate Similarity	NPC475913
0.8214	Intermediate Similarity	NPC239293
0.8208	Intermediate Similarity	NPC473199
0.8208	Intermediate Similarity	NPC181845
0.8198	Intermediate Similarity	NPC31797
0.819	Intermediate Similarity	NPC140723
0.819	Intermediate Similarity	NPC475701
0.819	Intermediate Similarity	NPC47113
0.819	Intermediate Similarity	NPC174367
0.8182	Intermediate Similarity	NPC171441
0.8182	Intermediate Similarity	NPC474410
0.8182	Intermediate Similarity	NPC219495
0.8182	Intermediate Similarity	NPC102619
0.8182	Intermediate Similarity	NPC293658
0.8174	Intermediate Similarity	NPC256983
0.8174	Intermediate Similarity	NPC476542
0.8174	Intermediate Similarity	NPC160084
0.8173	Intermediate Similarity	NPC160734
0.8173	Intermediate Similarity	NPC309425
0.8173	Intermediate Similarity	NPC88000
0.8173	Intermediate Similarity	NPC267510
0.8173	Intermediate Similarity	NPC47566
0.8173	Intermediate Similarity	NPC129372
0.8173	Intermediate Similarity	NPC4831
0.8173	Intermediate Similarity	NPC21568
0.8173	Intermediate Similarity	NPC285231
0.8173	Intermediate Similarity	NPC472023
0.8173	Intermediate Similarity	NPC470434
0.8165	Intermediate Similarity	NPC477073
0.8165	Intermediate Similarity	NPC274833
0.8163	Intermediate Similarity	NPC250687
0.8163	Intermediate Similarity	NPC48824
0.8163	Intermediate Similarity	NPC229407
0.8163	Intermediate Similarity	NPC254572
0.8158	Intermediate Similarity	NPC42675
0.8158	Intermediate Similarity	NPC475182
0.8158	Intermediate Similarity	NPC476675
0.8155	Intermediate Similarity	NPC234287
0.8155	Intermediate Similarity	NPC280825
0.8148	Intermediate Similarity	NPC42482
0.8148	Intermediate Similarity	NPC57362
0.8148	Intermediate Similarity	NPC40440
0.8148	Intermediate Similarity	NPC218853
0.8148	Intermediate Similarity	NPC204407
0.8148	Intermediate Similarity	NPC167383
0.8148	Intermediate Similarity	NPC237503
0.8148	Intermediate Similarity	NPC137917
0.8148	Intermediate Similarity	NPC306746
0.8142	Intermediate Similarity	NPC197003
0.8142	Intermediate Similarity	NPC319570
0.8142	Intermediate Similarity	NPC190939
0.8137	Intermediate Similarity	NPC256230
0.8136	Intermediate Similarity	NPC473593
0.8131	Intermediate Similarity	NPC113044
0.8131	Intermediate Similarity	NPC283849
0.8131	Intermediate Similarity	NPC305423
0.8131	Intermediate Similarity	NPC470432
0.8131	Intermediate Similarity	NPC287269
0.8131	Intermediate Similarity	NPC230507
0.8131	Intermediate Similarity	NPC161676
0.8131	Intermediate Similarity	NPC14704
0.8131	Intermediate Similarity	NPC283829
0.812	Intermediate Similarity	NPC42399

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 NPC121566 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1567
0.2-0.3	4196
0.3-0.4	2143
0.4-0.5	555
0.5-0.6	206
0.6-0.7	196
0.7-0.8	104
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.902	High Similarity	NPD6412	Phase 2
0.8407	Intermediate Similarity	NPD6370	Approved
0.823	Intermediate Similarity	NPD6059	Approved
0.823	Intermediate Similarity	NPD6054	Approved
0.812	Intermediate Similarity	NPD8293	Discontinued
0.8056	Intermediate Similarity	NPD6686	Approved
0.8051	Intermediate Similarity	NPD7736	Approved
0.8	Intermediate Similarity	NPD6016	Approved
0.8	Intermediate Similarity	NPD6015	Approved
0.7949	Intermediate Similarity	NPD7492	Approved
0.7931	Intermediate Similarity	NPD5988	Approved
0.7881	Intermediate Similarity	NPD6616	Approved
0.7881	Intermediate Similarity	NPD7507	Approved
0.7863	Intermediate Similarity	NPD6067	Discontinued
0.7843	Intermediate Similarity	NPD6399	Phase 3
0.7818	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD7078	Approved
0.7755	Intermediate Similarity	NPD4786	Approved
0.7714	Intermediate Similarity	NPD6084	Phase 2
0.7714	Intermediate Similarity	NPD6083	Phase 2
0.7699	Intermediate Similarity	NPD8133	Approved
0.7686	Intermediate Similarity	NPD7319	Approved
0.7652	Intermediate Similarity	NPD6009	Approved
0.7611	Intermediate Similarity	NPD6882	Approved
0.7603	Intermediate Similarity	NPD6033	Approved
0.7586	Intermediate Similarity	NPD7328	Approved
0.7586	Intermediate Similarity	NPD7327	Approved
0.7568	Intermediate Similarity	NPD7320	Approved
0.7551	Intermediate Similarity	NPD3667	Approved
0.7549	Intermediate Similarity	NPD4753	Phase 2
0.7545	Intermediate Similarity	NPD5739	Approved
0.7545	Intermediate Similarity	NPD6675	Approved
0.7545	Intermediate Similarity	NPD6402	Approved
0.7545	Intermediate Similarity	NPD7128	Approved
0.7544	Intermediate Similarity	NPD4632	Approved
0.7521	Intermediate Similarity	NPD7516	Approved
0.748	Intermediate Similarity	NPD5956	Approved
0.7458	Intermediate Similarity	NPD8294	Approved
0.7458	Intermediate Similarity	NPD8377	Approved
0.7458	Intermediate Similarity	NPD6319	Approved
0.7456	Intermediate Similarity	NPD8297	Approved
0.7455	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD8328	Phase 3
0.7411	Intermediate Similarity	NPD6881	Approved
0.7411	Intermediate Similarity	NPD6899	Approved
0.74	Intermediate Similarity	NPD3665	Phase 1
0.74	Intermediate Similarity	NPD3133	Approved
0.74	Intermediate Similarity	NPD3666	Approved
0.7395	Intermediate Similarity	NPD8296	Approved
0.7395	Intermediate Similarity	NPD8380	Approved
0.7395	Intermediate Similarity	NPD8379	Approved
0.7395	Intermediate Similarity	NPD8335	Approved
0.7395	Intermediate Similarity	NPD8033	Approved
0.7395	Intermediate Similarity	NPD8378	Approved
0.7395	Intermediate Similarity	NPD7503	Approved
0.7387	Intermediate Similarity	NPD6008	Approved
0.7383	Intermediate Similarity	NPD4755	Approved
0.7379	Intermediate Similarity	NPD5328	Approved
0.7358	Intermediate Similarity	NPD5695	Phase 3
0.7345	Intermediate Similarity	NPD6373	Approved
0.7345	Intermediate Similarity	NPD6372	Approved
0.7333	Intermediate Similarity	NPD4202	Approved
0.7321	Intermediate Similarity	NPD5701	Approved
0.7321	Intermediate Similarity	NPD5697	Approved
0.7315	Intermediate Similarity	NPD5696	Approved
0.7282	Intermediate Similarity	NPD6903	Approved
0.7282	Intermediate Similarity	NPD6672	Approved
0.7282	Intermediate Similarity	NPD5737	Approved
0.7281	Intermediate Similarity	NPD7102	Approved
0.7281	Intermediate Similarity	NPD4634	Approved
0.7281	Intermediate Similarity	NPD6883	Approved
0.7281	Intermediate Similarity	NPD7290	Approved
0.7255	Intermediate Similarity	NPD6409	Approved
0.7255	Intermediate Similarity	NPD6684	Approved
0.7255	Intermediate Similarity	NPD5330	Approved
0.7255	Intermediate Similarity	NPD7146	Approved
0.7255	Intermediate Similarity	NPD7334	Approved
0.7255	Intermediate Similarity	NPD3618	Phase 1
0.7255	Intermediate Similarity	NPD7521	Approved
0.7248	Intermediate Similarity	NPD5285	Approved
0.7248	Intermediate Similarity	NPD5286	Approved
0.7248	Intermediate Similarity	NPD4700	Approved
0.7248	Intermediate Similarity	NPD4696	Approved
0.7238	Intermediate Similarity	NPD6079	Approved
0.7217	Intermediate Similarity	NPD8130	Phase 1
0.7217	Intermediate Similarity	NPD6617	Approved
0.7217	Intermediate Similarity	NPD6869	Approved
0.7217	Intermediate Similarity	NPD6650	Approved
0.7217	Intermediate Similarity	NPD6847	Approved
0.7217	Intermediate Similarity	NPD6649	Approved
0.7203	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7115	Discovery
0.72	Intermediate Similarity	NPD4221	Approved
0.72	Intermediate Similarity	NPD4223	Phase 3
0.7196	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4629	Approved
0.7196	Intermediate Similarity	NPD5210	Approved
0.7193	Intermediate Similarity	NPD6014	Approved
0.7193	Intermediate Similarity	NPD6012	Approved
0.7193	Intermediate Similarity	NPD6013	Approved
0.7184	Intermediate Similarity	NPD7524	Approved
0.7157	Intermediate Similarity	NPD5329	Approved
0.7156	Intermediate Similarity	NPD7638	Approved
0.7131	Intermediate Similarity	NPD7604	Phase 2
0.7117	Intermediate Similarity	NPD5225	Approved
0.7117	Intermediate Similarity	NPD4633	Approved
0.7117	Intermediate Similarity	NPD5224	Approved
0.7117	Intermediate Similarity	NPD5211	Phase 2
0.7117	Intermediate Similarity	NPD5226	Approved
0.7115	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5983	Phase 2
0.7105	Intermediate Similarity	NPD6011	Approved
0.7091	Intermediate Similarity	NPD7640	Approved
0.7091	Intermediate Similarity	NPD7639	Approved
0.7087	Intermediate Similarity	NPD5279	Phase 3
0.7087	Intermediate Similarity	NPD6098	Approved
0.7069	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3668	Phase 3
0.7059	Intermediate Similarity	NPD4197	Approved
0.7059	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5174	Approved
0.7054	Intermediate Similarity	NPD5175	Approved
0.7048	Intermediate Similarity	NPD6673	Approved
0.7048	Intermediate Similarity	NPD6904	Approved
0.7048	Intermediate Similarity	NPD6080	Approved
0.7043	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5223	Approved
0.7016	Intermediate Similarity	NPD6336	Discontinued
0.7009	Intermediate Similarity	NPD6053	Discontinued
0.7	Intermediate Similarity	NPD7525	Registered
0.6991	Remote Similarity	NPD5141	Approved
0.6972	Remote Similarity	NPD5222	Approved
0.6972	Remote Similarity	NPD5221	Approved
0.6972	Remote Similarity	NPD4697	Phase 3
0.6972	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4788	Approved
0.6961	Remote Similarity	NPD6695	Phase 3
0.6944	Remote Similarity	NPD7748	Approved
0.693	Remote Similarity	NPD4768	Approved
0.693	Remote Similarity	NPD4767	Approved
0.6923	Remote Similarity	NPD4688	Approved
0.6923	Remote Similarity	NPD4138	Approved
0.6923	Remote Similarity	NPD4689	Approved
0.6923	Remote Similarity	NPD4693	Phase 3
0.6923	Remote Similarity	NPD4690	Approved
0.6923	Remote Similarity	NPD5205	Approved
0.6916	Remote Similarity	NPD5281	Approved
0.6916	Remote Similarity	NPD7515	Phase 2
0.6916	Remote Similarity	NPD8034	Phase 2
0.6916	Remote Similarity	NPD5284	Approved
0.6916	Remote Similarity	NPD8035	Phase 2
0.6909	Remote Similarity	NPD7902	Approved
0.6909	Remote Similarity	NPD5173	Approved
0.6903	Remote Similarity	NPD4754	Approved
0.6852	Remote Similarity	NPD8171	Discontinued
0.6837	Remote Similarity	NPD7339	Approved
0.6837	Remote Similarity	NPD6942	Approved
0.6833	Remote Similarity	NPD6274	Approved
0.6829	Remote Similarity	NPD8515	Approved
0.6829	Remote Similarity	NPD8517	Approved
0.6829	Remote Similarity	NPD8516	Approved
0.6829	Remote Similarity	NPD8513	Phase 3
0.6827	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5207	Approved
0.681	Remote Similarity	NPD5128	Approved
0.681	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4729	Approved
0.681	Remote Similarity	NPD4730	Approved
0.6803	Remote Similarity	NPD7101	Approved
0.6803	Remote Similarity	NPD4522	Approved
0.6803	Remote Similarity	NPD7100	Approved
0.6792	Remote Similarity	NPD5208	Approved
0.6789	Remote Similarity	NPD6001	Approved
0.6789	Remote Similarity	NPD5282	Discontinued
0.678	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6933	Approved
0.6762	Remote Similarity	NPD5280	Approved
0.6762	Remote Similarity	NPD4694	Approved
0.6762	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5690	Phase 2
0.6759	Remote Similarity	NPD6050	Approved
0.6759	Remote Similarity	NPD7637	Suspended
0.6759	Remote Similarity	NPD5693	Phase 1
0.6721	Remote Similarity	NPD6335	Approved
0.6698	Remote Similarity	NPD7750	Discontinued
0.6695	Remote Similarity	NPD5251	Approved
0.6695	Remote Similarity	NPD5249	Phase 3
0.6695	Remote Similarity	NPD5247	Approved
0.6695	Remote Similarity	NPD5250	Approved
0.6695	Remote Similarity	NPD5248	Approved
0.6695	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6909	Approved
0.6694	Remote Similarity	NPD6908	Approved
0.6694	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD8449	Approved
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD5692	Phase 3
0.6641	Remote Similarity	NPD8450	Suspended
0.6641	Remote Similarity	NPD8336	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