NPASS Compound

Natural Product: NPC24891

Natural Product ID	NPC24891
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VNSKBPUANWSMPF-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5318933
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 96100 0 0 0 0 0 0 0 0999 V2000 -9.2254 -0.4248 -0.8635 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8722 0.3546 0.3609 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0494 -0.4145 1.6215 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5150 0.9602 0.1949 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4490 -0.0336 -0.0160 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6307 -1.2802 -0.0569 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1724 0.4243 -0.1795 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0248 -0.4218 -0.3953 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5220 -0.1330 -1.7426 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0692 0.0193 -1.9871 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3448 0.6509 -0.7871 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9220 2.0153 -0.7285 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6736 -0.2421 0.3766 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6852 -0.3170 1.4526 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4669 0.6405 1.4575 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9488 1.1541 0.1167 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7832 2.6859 0.0521 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1604 0.5846 -1.0058 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6073 -0.8174 -1.2424 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0616 -1.0501 -1.0448 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9366 -0.2976 -0.4302 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3746 -0.6644 -0.3155 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8481 -1.6905 0.5861 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0331 -2.9816 0.3422 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2538 -2.0688 0.1294 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9526 -2.6469 1.3434 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0882 -1.0034 -0.4350 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4350 -0.0317 -1.3938 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2545 0.5380 -0.5538 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4709 1.4990 -1.3628 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1700 1.9950 -0.8288 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4365 1.0035 0.0819 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8912 1.3861 1.4765 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9774 1.0978 0.5763 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0336 0.7521 1.7532 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7508 2.2410 0.2612 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8280 -1.5508 1.9336 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1303 -0.2197 0.7858 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2565 -1.5231 1.6267 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5967 0.8488 1.6687 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8065 -1.4373 -0.8962 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8181 0.1522 -1.7433 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3290 -0.4150 -1.0109 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5983 1.2205 0.4009 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1599 -0.4790 1.8109 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6979 -1.4627 1.5783 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6471 0.1394 2.4870 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4999 1.6663 -0.6595 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2131 1.5770 1.0858 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4827 -1.4613 -0.3850 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0773 0.7331 -2.2293 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8587 -0.9776 -2.4339 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9198 0.7390 -2.8182 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6448 -0.9246 -2.2907 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9536 2.0550 -1.2314 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3838 2.7516 -1.3463 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1918 2.3714 0.2896 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6578 -1.2897 -0.1034 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3408 -1.3793 1.6785 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2387 -0.1041 2.4248 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2473 0.1281 2.0522 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1873 1.5558 2.0629 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8827 3.0555 -0.9790 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0690 3.0515 0.6289 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6524 3.2012 0.5801 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3228 1.1618 -1.9422 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1206 -1.6116 -0.6578 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3442 -1.0903 -2.3151 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5040 -1.9816 -1.4723 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5515 -1.2537 -1.3165 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2182 -3.4045 -0.6396 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0039 -2.8843 0.6769 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5038 -3.7162 1.0671 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2213 -2.9231 -0.6117 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5716 -3.6474 1.6139 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8082 -1.9038 2.1721 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0593 -2.6704 1.1704 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6250 -0.3849 0.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9126 -1.4861 -1.0111 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0530 -0.5840 -2.2698 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1573 0.7419 -1.6439 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2698 1.0076 -2.3575 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0736 2.4106 -1.6507 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 2.9304 -0.2886 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5113 2.2311 -1.6832 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6243 2.2611 1.4589 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0833 1.9064 2.0854 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2119 0.5753 2.1101 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3388 2.6772 0.9323 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9639 -1.7754 2.3710 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3153 -1.8536 1.6155 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6627 -2.3193 1.1328 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9823 -1.3480 2.6658 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2368 1.6462 1.1810 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8863 1.3635 2.3109 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3505 0.4199 2.4085 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 29 34 1 0 34 35 2 0 34 36 1 0 23 37 1 0 13 38 1 0 38 39 1 0 38 40 1 0 38 8 1 0 18 11 1 0 32 21 1 0 32 16 1 0 29 22 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 0 3 45 1 0 3 46 1 0 3 47 1 0 4 48 1 0 4 49 1 0 8 50 1 0 9 51 1 0 9 52 1 0 10 53 1 0 10 54 1 0 12 55 1 0 12 56 1 0 12 57 1 0 13 58 1 0 14 59 1 0 14 60 1 0 15 61 1 0 15 62 1 0 17 63 1 0 17 64 1 0 17 65 1 0 18 66 1 0 19 67 1 0 19 68 1 0 20 69 1 0 22 70 1 0 24 71 1 0 24 72 1 0 24 73 1 0 25 74 1 0 26 75 1 0 26 76 1 0 26 77 1 0 27 78 1 0 27 79 1 0 28 80 1 0 28 81 1 0 30 82 1 0 30 83 1 0 31 84 1 0 31 85 1 0 33 86 1 0 33 87 1 0 33 88 1 0 36 89 1 0 37 90 1 0 39 91 1 0 39 92 1 0 39 93 1 0 40 94 1 0 40 95 1 0 40 96 1 0 M END

Standard InCHIKey	VNSKBPUANWSMPF-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C35H56O5/c1-21(2)20-27(36)40-26-14-15-31(6)24(30(26,4)5)13-16-33(8)25(31)11-10-23-28-34(9,39)22(3)12-17-35(28,29(37)38)19-18-32(23,33)7/h10,21-22,24-26,28,39H,11-20H2,1-9H3,(H,37,38)
SMILES	CC(C)CC(=O)OC1CCC2(C)C(CCC3(C)C2CC=C2C4C(C)(C(C)CCC4(CCC32C)C(=O)O)O)C1(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	556.41	Volume:	607.175 ? Van der Waals volume.
Dense:	0.916	LogP:	4.821 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.004 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.779 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	28.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.273	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.968	Fsp³:	0.886
MCE-18:	109.455 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.185	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.201 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.302	Promiscuous compounds:	0.006

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.992	MDCK Permeability:	-4.771
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.567 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.813	MRP1:	1.0
Plasma Protein Binding (PPB):	96.636%	Volume Distribution (VD):	0.048
Fu:	4.159% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.003
OATP1B3 inhibitor:	0.728	BCRP inhibitor:	0.0
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.049	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.909	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.936	CYP3A4-substrate:	0.0
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.476
HLM stability:	0.694 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.539

Half-life (T1/2):

1.373

ADMET: Toxicity

hERG Blockers:	0.046	hERG Blockers (10um):	0.135
Human Hepatotoxicity (H-HT):	0.501	Drug-induced Liver Injury (DILI):	0.093
AMES Toxicity:	0.025	Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.535	Skin Sensitization:	0.732
Carcinogencity:	0.234	Eye Corrosion:	0.002
Eye Irritation:	0.119	Respiratory Toxicity:	0.495
Drug-induced Neurotoxicity:	0.099	Ototoxicity:	0.961
Hematotoxicity:	0.243	Drug-induced Nephrotoxicity:	0.557
Genotoxicity:	0.003	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.039	Hek293 Cytotoxicity:	0.073
BCF:	1.743 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.911 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.176 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.536 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[10869197]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812212]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33780581]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36270431]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38257257]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38893531]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39104562]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9834145]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1859	Lantana camara	Species	Verbenaceae	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	Organism Name	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC24891 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	18199
0.1-0.2	26128
0.2-0.3	4371
0.3-0.4	845
0.4-0.5	252
0.5-0.6	29
0.6-0.7	27
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7568	Intermediate Similarity	NPC233012
0.7333	Intermediate Similarity	NPC327179
0.6892	Remote Similarity	NPC148964
0.6883	Remote Similarity	NPC54909
0.6849	Remote Similarity	NPC202728
0.6849	Remote Similarity	NPC158059
0.68	Remote Similarity	NPC187933
0.6622	Remote Similarity	NPC136697
0.6591	Remote Similarity	NPC482052
0.6579	Remote Similarity	NPC157113
0.6533	Remote Similarity	NPC485589
0.6533	Remote Similarity	NPC191412
0.6533	Remote Similarity	NPC114159
0.6533	Remote Similarity	NPC6818
0.6447	Remote Similarity	NPC62516
0.64	Remote Similarity	NPC259733
0.64	Remote Similarity	NPC158371
0.64	Remote Similarity	NPC207922
0.64	Remote Similarity	NPC120840
0.6316	Remote Similarity	NPC247139
0.6203	Remote Similarity	NPC485586
0.6203	Remote Similarity	NPC485588
0.6203	Remote Similarity	NPC603658
0.6154	Remote Similarity	NPC25491
0.6104	Remote Similarity	NPC35239
0.6104	Remote Similarity	NPC132824
0.6053	Remote Similarity	NPC235053
0.6026	Remote Similarity	NPC118964
0.6022	Remote Similarity	NPC482051
0.5974	Remote Similarity	NPC256247
0.5949	Remote Similarity	NPC147232
0.5949	Remote Similarity	NPC284865
0.5854	Remote Similarity	NPC96693
0.5833	Remote Similarity	NPC600756
0.5732	Remote Similarity	NPC230151
0.5714	Remote Similarity	NPC481234
0.5714	Remote Similarity	NPC479431
0.5696	Remote Similarity	NPC118519
0.5625	Remote Similarity	NPC137072
0.5556	Remote Similarity	NPC488521
0.5532	Remote Similarity	NPC172311
0.5446	Remote Similarity	NPC481235
0.5444	Remote Similarity	NPC485587
0.5385	Remote Similarity	NPC173569
0.5287	Remote Similarity	NPC485585
0.5281	Remote Similarity	NPC283849
0.5281	Remote Similarity	NPC485882
0.5258	Remote Similarity	NPC482049
0.5258	Remote Similarity	NPC482050
0.519	Remote Similarity	NPC191965
0.5181	Remote Similarity	NPC296164
0.5161	Remote Similarity	NPC473538
0.5122	Remote Similarity	NPC113989
0.5111	Remote Similarity	NPC606107
0.506	Remote Similarity	NPC608622
0.5055	Remote Similarity	NPC177246
0.5053	Remote Similarity	NPC475611
0.5051	Remote Similarity	NPC610795

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC24891 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5541
0.1-0.2	3530
0.2-0.3	66
0.3-0.4	9
0.4-0.5	4
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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